Ethanol → Ethyl 2-hydroxy-2-phenylpropanoate
Reaction equation
[C:1]1([C:7]([CH3:12])([OH:11])[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[CH2:18](O)[CH3:19]>CCOCC>[C:1]1([C:7]([CH3:12])([OH:11])[C:8]([O:10][CH2:18][CH3:19])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
(±)-Phenyllactic acid (4.96 g) and 1/2 ml concentrated sulfuric acid in 150 ml absolute ethanol is refluxed for 18 hours. Solvent is stripped, the residue is dissolved in ether, and extracted with saturated sodium bicarbonate solution. The ether is dried, filtered, and stripped to leave (±)-ethyl phenyllactate. NMR (CDCl3): δ1.3 (t, 3H), 3.0 (d of d, 1H), 3.1 (d of d, 1H), 4.2 (q, 2H), 4.4 (d of d, 1H), 7.3 (m, 5H).
Workup
- extractionextracted with saturated sodium bicarbonate solution
- dry with materialThe ether is dried
- filtrationfiltered
Sources & evidence
- ORD record
- ord-a2e094f4293f41d5bfddf16caeeec860
- Source dataset
- uspto-grants-1995_03
- Patent number
- US05401772
Reaction notes
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