Ethanol → Ethyl 4-hydroxyhydrocinnamate
Reaction equation
S(=O)(=O)(O)O.[OH:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:9][CH:8]=1.[CH2:18](O)[CH3:19]>>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][CH:12]=1Participants
Procedure
Sulfuric acid (230 g) was dropped under stirring for 10 minutes to an ethanol solution (1500 mL) of 3-(4-hydroxyphenyl)propionic acid (1150 g), and refluxed successively for 5 hours. The reaction mixture was concentrated and the obtained concentrated solution was poured into water (1,000 mL) and stirred with addition of ethyl acetate. After separation of the solution, an ethyl acetate layer was neutralized with an aqueous solution of a saturated sodium carbonate, washed with a small amount of water and then dried over anhydrous magnesium sulfate. Ethyl acetate and unreactcd ingredients were distilled off from the ethyl acetate layer to obtain concentrates (1,400 g). The concentrates were purified by distillation under a reduced pressure to obtain ethyl 3-(4-hydroxyphenyl)propionate (1,144 g). The boiling point was 160° C./4.0 hPa.
Workup
- temperaturerefluxed successively for 5 hours
- concentrationThe reaction mixture was concentrated
- additionthe obtained concentrated solution was poured into water (1,000 mL)
- customAfter separation of the solution
- washwashed with a small amount of water
- dry with materialdried over anhydrous magnesium sulfate
- distillationEthyl acetate and unreactcd ingredients were distilled off from the ethyl acetate layer
- customto obtain concentrates (1,400 g)
- distillationThe concentrates were purified by distillation under a reduced pressure
Sources & evidence
- ORD record
- ord-4aab69c2434b441a8d3d19dc38fec6f6
- Source dataset
- uspto-grants-2011_03
- Patent number
- USRE042221E1
Reaction notes
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