3,5-diacetoxybenzoic acid |
| Reaction ID DSp36-2 | 3,5-diacetoxybenzoic acid |
| Researcher | Dustin Sprouse | | Reaction Type | acid chloride formation | | Solvent | benzene | | Limiting Reactant | 1 M | | Precipitate | No | | Comments | drop of DMF; 80C 2h then evaporation | | Reference | http://precedings.nature.com/documents/4685/version/1 |
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 | + |  | → |  | | | | |
| 3,5-diacetoxybenzoic acid | | thionyl chloride | | 3,5-diacetoxybenzoyl chloride | | | | |
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| Reaction ID DSp37 | 3,5-diacetoxybenzoic acid |
| Researcher | Dustin Sprouse | | Reaction Type | acid chloride formation | | Solvent | benzene | | Limiting Reactant | 1 M | | Precipitate | No | | Yield | 45 % | | Comments | drop of DMF; 80C 2h? then evaporation then silica plug with toluene | | Reference | http://precedings.nature.com/documents/4685/version/1 |
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| + | | → | | | | | |
| 3,5-diacetoxybenzoic acid | | thionyl chloride | | 3,5-diacetoxybenzoyl chloride | | | | |
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3,5-diacetoxybenzoyl chloride |
| Reaction ID DSp39 | 3,5-diacetoxybenzoyl chloride |
| Researcher | Dustin Sprouse | | Reaction Type | Heck coupling | | Solvent | p-xylene | | Limiting Reactant | 0.4 M | | Precipitate | No | | Comments | N-ethylmorpholine Pd(OAc)2 and imidazolium cat; 4h 115-140C; chromatography eluted too fast | | Reference | http://precedings.nature.com/documents/4685/version/1 |
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| + |  | → |  | | | | |
| 3,5-diacetoxybenzoyl chloride | | 4-acetoxystyrene | | resveratrol triacetate | | | | |
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| Reaction ID DSp40 | 3,5-diacetoxybenzoyl chloride |
| Researcher | Dustin Sprouse | | Reaction Type | Heck coupling | | Solvent | p-xylene | | Limiting Reactant | 0.4 M | | Precipitate | No | | Comments | N-ethylmorpholine Pd(OAc)2 and imidazolium cat; 4h 120-125C; chromatography eluted too fast | | Reference | http://precedings.nature.com/documents/4685/version/1 |
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| + | | → | | | | | |
| 3,5-diacetoxybenzoyl chloride | | 4-acetoxystyrene | | resveratrol triacetate | | | | |
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| Reaction ID DSp41 | 3,5-diacetoxybenzoyl chloride |
| Researcher | Dustin Sprouse | | Reaction Type | Heck coupling | | Solvent | p-xylene | | Limiting Reactant | 0.4 M | | Precipitate | No | | Yield | 25 % | | Comments | N-ethylmorpholine Pd(OAc)2 and imidazolium cat; 4h 120-125C; chromatography eluted slower - product has impurities | | Reference | http://precedings.nature.com/documents/4685/version/1 |
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| + | | → | | | | | |
| 3,5-diacetoxybenzoyl chloride | | 4-acetoxystyrene | | resveratrol triacetate | | | | |
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3,5-dihydroxybenzoic acid |
| Reaction ID DSp35 | 3,5-dihydroxybenzoic acid |
| Researcher | Dustin Sprouse | | Reaction Type | acylation | | Solvent | ethyl acetate | | Limiting Reactant | 0.4 M | | Precipitate | No | | Yield | 62 % | | Comments | with pyridine(2 eq) at 0C to rt 4h then add formic acid and wash | | Reference | http://precedings.nature.com/documents/4685/version/1 |
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| 3,5-dihydroxybenzoic acid | | acetic anhydride | | 3,5-diacetoxybenzoic acid | | | | |
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| Reaction ID DSp36-1 | 3,5-dihydroxybenzoic acid |
| Researcher | Dustin Sprouse | | Reaction Type | acylation | | Solvent | ethyl acetate | | Limiting Reactant | 0.4 M | | Precipitate | No | | Yield | 85 % | | Comments | with pyridine(2 eq) at 0C to rt 4h then add formic acid and wash - less washing solvents gave higher yield | | Reference | http://precedings.nature.com/documents/4685/version/1 |
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| + | | → | | | | | |
| 3,5-dihydroxybenzoic acid | | acetic anhydride | | 3,5-diacetoxybenzoic acid | | | | |
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p-anisaldehyde |
| Reaction ID DSp31 | p-anisaldehyde |
| Researcher | Dustin Sprouse | | Reaction Type | Grignard | | Solvent | diethyl ether | | Limiting Reactant | 0.6 M | | Precipitate | No | | Comments | Mg then aldehyde then 3N HCl; mixtures obtained | | Reference | http://precedings.nature.com/documents/4685/version/1 |
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 | + |  | → |  | | | | |
| benzyl chloride | | p-anisaldehyde | | p-methoxystilbene | | | | |
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resveratrol triacetate |
| Reaction ID DSp42 | resveratrol triacetate |
| Researcher | Dustin Sprouse | | Reaction Type | hydrolysis | | Solvent | THF/water | | Limiting Reactant | 0.01 M | | Precipitate | No | | Comments | NaOH 2h rt then HCl then ethyl acetate extraction | | Reference | http://precedings.nature.com/documents/4685/version/1 |
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 | + | | → |  | | | | |
| NaOH | | resveratrol triacetate | | resveratrol | | | | |
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| Reaction ID DSp43 | resveratrol triacetate |
| Researcher | Dustin Sprouse | | Reaction Type | hydrolysis | | Solvent | THF/water | | Limiting Reactant | 0.03 M | | Precipitate | No | | Yield | - % | | Comments | NaOH (large xs) 2h rt then HCl then ethyl acetate extraction - starting material and product impure | | Reference | http://precedings.nature.com/documents/4685/version/1 |
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| + | | → | | | | | |
| NaOH | | resveratrol triacetate | | resveratrol | | | | |
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