ONS Challenge

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Reactions 
Reaction ID UCEXP286
 
ResearcherMatthew McBride
Reaction Typealdol condensation
Solventmethanol
Limiting Reactant0.011 M
PrecipitateYes
Yield19 %
CommentsNaOH (1.3M - 81eq to acetone) in methanol rt 3 days then filtered then recrystallized from benzene
Referencehttp://usefulchem.wikispaces.com/EXP286
Solvent SelectionOptimal Solvent Prediction
 
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acetone phenanthrene-9-carboxaldehyde (1E4E)-1,5-Di(9-phenanthryl)-1,4-pentadien-3-one    

Reaction ID CRSEXP035C1
 
ResearcherMatthew McBride
Reaction Typesalicylaldehyde propylamine
Solvent - 
Limiting Reactant -  M
PrecipitateYes
Product - 
CommentsInsolubility event occurred
Referencehttp://chemrs.wikispaces.com/CRSEXP035
 
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propylamine salicylaldehyde 2-[(E)-(Propylimino)methyl]phenol    

Reaction ID CRSEXP035D1
 
ResearcherMatthew McBride
Reaction Typesalicylaldehyde benzene
Solvent - 
Limiting Reactant -  M
PrecipitateNo
Comments - 
Referencehttp://chemrs.wikispaces.com/CRSEXP035
 
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benzene salicylaldehyde 6H12H-Dibenzo[bf][15]dioxocine    

Reaction ID ONSEXP351
 
ResearcherMatthew McBride
Reaction Typerecrystallization
Solventn-hexane
Limiting Reactant0.25 M
Precipitateyes
Yield59 %
Commentsre-crystallized in 10mL test tube with benzoic acid (1.83 mmol 0.2229 g); water bath used to heat solution to boiling; sintered glass funnel was used to suction filter; washed 1x with hexane and dried the crystals over suction (25 min)
Referencehttp://onschallenge.wikispaces.com/EXP351
Solvent SelectionOptimal Solvent Prediction
 
      
benzoic acid benzoic acid      

Reaction ID ONSEXP359
 
ResearcherMatthew McBride
Reaction Typerecrystallization
Solventwater
Limiting Reactant1.35 M
Precipitateyes
Yield67 %
Commentsre-crystallized in 10mL test tube with benzoic acid (2.12 mmol 0.2584 g); ethylene glycol bath used to heat solution to 100C; cooled on ice for 15 minutes; sintered glass funnel used to suction filter; washed 3x with pentane; air dried for 10 minutes; water in HNMR spectrum so pentane wash did not remove the water solvent
Referencehttp://onschallenge.wikispaces.com/EXP359
Solvent SelectionOptimal Solvent Prediction
 
      
benzoic acid benzoic acid      

Reaction ID ONSEXP342-A
 
ResearcherMatthew McBride
Reaction Typerecrystallization
Solvent1-octanol
Limiting Reactant2.2 M
PrecipitateNo
Commentscaffeine (1.0135 g 5.3mmol) would not dissolve into the 1-octanol; too large of an Erlenmeyer flask was used (25mL)
Referencehttp://onschallenge.wikispaces.com/EXP342
Solvent SelectionOptimal Solvent Prediction
 
      
caffeine caffeine      

Reaction ID ONSEXP342-B
 
ResearcherMatthew McBride
Reaction Typerecrystallization
Solvent1-octanol
Limiting Reactant0.77 M
PrecipitateNo
Commentscaffeine (1.0251g 5.3mmol) re-crystallized in Erlenmeyer flask on hot plate; cooled to room temperature; crystals did not separate from 1-octanol so none of the 1-octanol could be removed prior to pentane wash
Referencehttp://onschallenge.wikispaces.com/EXP342
Solvent SelectionOptimal Solvent Prediction
 
      
caffeine caffeine      

Reaction ID ONSEXP342-C
 
ResearcherMatthew McBride
Reaction Typerecrystallization
Solvent1-octanol
Limiting Reactant0.26 M
PrecipitateYes
Yield77 %
Commentscaffeine (1.03 g 5.3mmol) re-crystallized in Erlenmeyer flask on hot plate; cooled to room temperature; filtered on Butcher funnel; washed 5x with pentane
Referencehttp://onschallenge.wikispaces.com/EXP342
Solvent SelectionOptimal Solvent Prediction
 
      
caffeine caffeine      

Reaction ID ONSEXP343-1
 
ResearcherMatthew McBride
Reaction Typerecrystallization
Solvent1-octanol
Limiting Reactant1.53 M
PrecipitateNo
Comments10mL test tube with caffeine (0.25g 1.3mmol); crystals did not enter the solution at 160C
Referencehttp://onschallenge.wikispaces.com/EXP343
Solvent SelectionOptimal Solvent Prediction
 
      
caffeine caffeine      

Reaction ID ONSEXP343-2
 
ResearcherMatthew McBride
Reaction Typerecrystallization
Solvent1-octanol
Limiting Reactant0.77 M
PrecipitateNo
Comments10mL test tube with caffeine (0.25g 1.3mmol);sample contaminated with water; sample aborted
Referencehttp://onschallenge.wikispaces.com/EXP343
Solvent SelectionOptimal Solvent Prediction
 
      
caffeine caffeine      

Reaction ID ONSEXP343-3
 
ResearcherMatthew McBride
Reaction Typerecrystallization
Solvent1-octanol
Limiting Reactant0.25 M
PrecipitateYes
Yield89 %
Comments10mL test tube with caffeine (0.25g 1.3mmol); centrifuge method was used to wash the crystals 12x with 1.5g of pentane; removed 54% of 1-octanol before washing with pentane
Referencehttp://onschallenge.wikispaces.com/EXP343
Solvent SelectionOptimal Solvent Prediction
 
      
caffeine caffeine      

Reaction ID ONSEXP346
 
ResearcherMatthew McBride
Reaction Typerecrystallization
Solvent1-octanol
Limiting Reactant0.75 M
PrecipitateNo
Commentsre-crystallization performed in a sinter glass funnel; heated with a heating mantel; crystals blocked filter so no liquid could be removed
Referencehttp://onschallenge.wikispaces.com/EXP346
Solvent SelectionOptimal Solvent Prediction
 
      
caffeine caffeine      

Reaction ID ONSEXP358
 
ResearcherMatthew McBride
Reaction Typerecrystallization
Solventtoluene
Limiting Reactant0.24 M
Precipitateyes
Yield80 %
Commentsre-crystallized in 10mL test tube with caffeine(1.08 mmol 0.2520 g); ethylene glycol bath used to heat solution to 110C; cooled on ice for 20 minutes; sintered glass funnel used to suction filter; washed 3x with pentane; air dried for 10 minutes; verified by HNMR that no toluene was present in the product crystals
Referencehttp://onschallenge.wikispaces.com/EXP358
Solvent SelectionOptimal Solvent Prediction
 
      
caffeine caffeine      

Reaction ID ONSEXP352
 
ResearcherMatthew McBride
Reaction Typerecrystallization
Solventcyclohexane
Limiting Reactant0.23 M
Precipitateyes
Yield88 %
Commentsre-crystallized in 10mL test tube with cinnamic acid (1.67 mmol 0.2472 g); water bath used to heat solution to boiling; sintered glass funnel was used to suction filter; washed 1x with cyclohexane and dried over suction (35 min)
Referencehttp://onschallenge.wikispaces.com/EXP352
Solvent SelectionOptimal Solvent Prediction
 
      
cinnamic acid cinnamic acid      

Reaction ID CRSEXP027-2
 
ResearcherMatthew McBride
Reaction Typeacetone piperidine
Solvent - 
Limiting Reactant -  M
PrecipitateNo
Yield -  %
CommentsFormed Diacetone Alcohol
Referencehttp://chemrs.wikispaces.com/CRSEXP027
 
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acetone piperidine Diacetone alcohol    

Reaction ID ONSEXP269
 
ResearcherMatthew McBride
Reaction Typealdol condensation
Solventethanol/water (1:6)vol
Limiting Reactant0.43 M
PrecipitateNo
CommentsUsed KOH as base catalyst (1.8M) but KOH was not fully dissolved in water before addition of the ethanol; benzaldehyde did not fully dissolve into the ethanol before addition of acetone.
Referencehttp://onschallenge.wikispaces.com/EXP269
Solvent SelectionOptimal Solvent Prediction
 
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acetone benzaldehyde dibenzalacetone    

Reaction ID ONSEXP274
 
ResearcherMatthew McBride
Reaction Typealdol condensation
Solventethanol/water (1:2)vol
Limiting Reactant0.33 M
PrecipitateYes
Yield45 %
CommentsProduct was a dark orange following recrystallization from ethanol and was very hard and not crystals. Used KOH as base catalyst (3M).
Referencehttp://onschallenge.wikispaces.com/EXP274
Solvent SelectionOptimal Solvent Prediction
 
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acetone benzaldehyde dibenzalacetone    

Reaction ID ONSEXP278
 
ResearcherMatthew McBride
Reaction Typealdol condensation
Solventethanol/water (1:2)vol
Limiting Reactant0.33 M
PrecipitateNo
CommentsOrange bubble formed on top of solution rather than crystals. Too little ethanol was used to dissolve the benzaldehyde. Used KOH (0.3M) as base catalyst.
Referencehttp://onschallenge.wikispaces.com/EXP278
Solvent SelectionOptimal Solvent Prediction
 
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acetone benzaldehyde dibenzalacetone    

Reaction ID ONSEXP279
 
ResearcherMatthew McBride
Reaction Typealdol condensation
Solventethanol/water (1:1)vol
Limiting Reactant1.2 M
PrecipitateYes
Yield55 %
CommentsRecrystallized product from ethyl acetate. Used KOH (1.5M) as base catalyst.
Referencehttp://onschallenge.wikispaces.com/EXP279
Solvent SelectionOptimal Solvent Prediction
 
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acetone benzaldehyde dibenzalacetone    

Reaction ID ONSEXP302
 
ResearcherMatthew McBride
Reaction Typealdol condensation
Solventethanol/water (1:1)vol
Limiting Reactant1.1 M
PrecipitateNo
CommentsObtained crude product but no product recovered from recrystallization from ethanol. Used KOH (1.5M) as base catalyst.
Referencehttp://onschallenge.wikispaces.com/EXP302
Solvent SelectionOptimal Solvent Prediction
 
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acetone benzaldehyde dibenzalacetone    

Reaction ID ONSEXP307
 
ResearcherMatthew McBride
Reaction Typealdol condensation
Solventethanol/water (1:1)vol
Limiting Reactant1.1 M
PrecipitateYes
Yield39 %
CommentsSome impurity present in the product. Product was recrystallized from ethanol. Used KOH (1.5M) as base catalyst.
Referencehttp://onschallenge.wikispaces.com/EXP307
Solvent SelectionOptimal Solvent Prediction
 
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acetone benzaldehyde dibenzalacetone    

Reaction ID ONSEXP314
 
ResearcherMatthew McBride
Reaction Typealdol condensation
Solventethanol
Limiting Reactant0.667 M
PrecipitateYes
Yield8 %
CommentsSodium Carbonate (white solid) formed from NaOH (catalyst) reacting with air and had to be removed. Product was recrystallized from ethanol. Used NaOH as base catalyst.
Referencehttp://onschallenge.wikispaces.com/EXP314
Solvent SelectionOptimal Solvent Prediction
 
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acetone benzaldehyde dibenzalacetone    

Reaction ID ONSEXP321
 
ResearcherMatthew McBride
Reaction Typerecrystallization
Solventethanol
Limiting Reactant1.23 M
Precipitateyes
Yield77 %
Commentsre-crystallized in a Erlenmeyer flask on hot plate; cooled to room temp; filtered on Buchner funnel
Referencehttp://onschallenge.wikispaces.com/EXP321
Solvent SelectionOptimal Solvent Prediction
 
      
dibenzalacetone dibenzalacetone      

Reaction ID ONSEXP322
 
ResearcherMatthew McBride
Reaction Typerecrystallization
Solventethanol/water(50:50)vol
Limiting Reactant0.04 M
Precipitateyes
Yield76 %
Commentsre-crystallized in a Erlenmeyer flask on hot plate; cooled to room temp; filtered on Buchner funnel; small clump of crystals that did not fully dissolve into the solution
Referencehttp://onschallenge.wikispaces.com/EXP322
Solvent SelectionOptimal Solvent Prediction
 
      
dibenzalacetone dibenzalacetone      

Reaction ID ONSEXP325
 
ResearcherMatthew McBride
Reaction Typerecrystallization
Solventn-hexane
Limiting Reactant0.1 M
Precipitateyes
Yield64 %
Commentsre-crystallized in a Erlenmeyer flask on hot plate; cooled to room temp; filtered on Buchner funnel; crystals were stuck to bottom and sides of flask
Referencehttp://onschallenge.wikispaces.com/EXP325
Solvent SelectionOptimal Solvent Prediction
 
      
dibenzalacetone dibenzalacetone      

Reaction ID ONSEXP353
 
ResearcherMatthew McBride
Reaction Typerecrystallization
Solventethanol
Limiting Reactant0.74 M
Precipitateyes
Yield69 %
Commentsre-crystallized in 10mL test tube with dibenzalacetone (1.11 mmol 0.2600 g); water bath used to heat solution to 75C; sintered glass funnel was used to suction filter; washed 1x with ethanol and dried over suction (40 min)
Referencehttp://onschallenge.wikispaces.com/EXP353
Solvent SelectionOptimal Solvent Prediction
 
      
dibenzalacetone dibenzalacetone      

Reaction ID UCEXP281
 
ResearcherMatthew McBride
Reaction Typealdol condensation
Solventethanol
Limiting Reactant1.33 M
PrecipitateNo
CommentsPiperidine was used to catalyze the reaction but no product formed
Referencehttp://usefulchem.wikispaces.com/EXP281
Solvent SelectionOptimal Solvent Prediction
 
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acetone benzaldehyde dibenzalacetone    

Reaction ID UCEXP282
 
ResearcherMatthew McBride
Reaction Typealdol condensation
Solventethanol/water (1:1)vol
Limiting Reactant1 M
PrecipitateYes
Yield51 %
CommentsProduct was a dark orange following recrystallization from ethanol and impure likely from sodium carbonate. NaOH used as catalyst.
Referencehttp://usefulchem.wikispaces.com/EXP282
Solvent SelectionOptimal Solvent Prediction
 
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acetone benzaldehyde dibenzalacetone    

Reaction ID UCEXP283
 
ResearcherMatthew McBride
Reaction Typealdol condensation
Solventethanol
Limiting Reactant0.9 M
PrecipitateNo
CommentsPiperidine was used as catalyst but no product formed
Referencehttp://usefulchem.wikispaces.com/EXP283
Solvent SelectionOptimal Solvent Prediction
 
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acetone benzaldehyde dibenzalacetone    

Reaction ID UCEXP284
 
ResearcherMatthew McBride
Reaction Typealdol condensation
Solventethanol/water (1:1)vol
Limiting Reactant0.17 M
PrecipitateYes
Yield90.6 %
CommentsNaOH catalyst (1.57 eq to acetone); 2.87 eq benzaldehyde to acetone; 30 min rt then filtered; washed 1x with 2-3mL of 1:1 ethanol/water; dried over suction for 25 min; no re-crystallization required
Referencehttp://usefulchem.wikispaces.com/EXP284
Solvent SelectionOptimal Solvent Prediction
 
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acetone benzaldehyde dibenzalacetone    

Reaction ID UCEXP285
 
ResearcherMatthew McBride
Reaction Typealdol condensation
Solventethanol/water (1:1)vol
Limiting Reactant0.19 M
PrecipitateYes
Yield84.7 %
CommentsNaOH catalyst (1.17 eq to acetone); 2.52 eq benzaldehyde to acetone; 40 min rt then flitered; washed 1x with 1:1 ethanol/water; dried over suction for 40 min; no re-crystallization completed but slight ethanol impurity present in HNMR spectrum
Referencehttp://usefulchem.wikispaces.com/EXP285
Solvent SelectionOptimal Solvent Prediction
 
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acetone benzaldehyde dibenzalacetone    

Reaction ID CRSEXP027-1
 
ResearcherMatthew McBride
Reaction Typeacetone piperidine
Solvent - 
Limiting Reactant -  M
PrecipitateNo
CommentsDid not form Mesityl oxide
Referencehttp://chemrs.wikispaces.com/CRSEXP027
 
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acetone piperidine Mesityl oxide    

Reaction ID CRSEXP035B1
 
ResearcherMatthew McBride
Reaction Typesalicylaldehyde ethanol
Solvent - 
Limiting Reactant -  M
PrecipitateNo
Yield -  %
CommentsAcetal was formed
Referencehttp://chemrs.wikispaces.com/CRSEXP035
 
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ethanol salicylaldehyde salicylaldehyde ethanol acetal    

Reaction ID CRSEXP035B2
 
ResearcherMatthew McBride
Reaction Typesalicylaldehyde ethanol
Solvent - 
Limiting Reactant -  M
PrecipitateNo
Yield -  %
CommentsHemiacetal was formed
Referencehttp://chemrs.wikispaces.com/CRSEXP035
 
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ethanol salicylaldehyde salicylaldehyde ethanol hemiacetal    

Reaction ID CRSEXP035A1
 
ResearcherMatthew McBride
Reaction Typesalicylaldehyde methanol
Solvent - 
Limiting Reactant -  M
PrecipitateNo
Yield -  %
CommentsAcetal was formed
Referencehttp://chemrs.wikispaces.com/CRSEXP035
 
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methanol salicylaldehyde salicylaldehyde methanol acetal    

Reaction ID CRSEXP035A2
 
ResearcherMatthew McBride
Reaction Typesalicylaldehyde methanol
Solvent - 
Limiting Reactant -  M
PrecipitateNo
Yield -  %
CommentsHemiacetal was formed
Referencehttp://chemrs.wikispaces.com/CRSEXP035
 
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methanol salicylaldehyde salicylaldehyde methanol hemiacetal    

36 Reactions Found