Ethanol → Ethyl 2-hydroxy-2-phenylpropanoate

HRID 866002

Reaction equation

HRID 866002 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]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 1303Atrolactic acid

Product 1

HCID 6429709Ethyl 2-hydroxy-2-phenylpropanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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

  1. extractionextracted with saturated sodium bicarbonate solution
  2. dry with materialThe ether is dried
  3. filtrationfiltered

Sources & evidence

ORD record
ord-4da8ca9e64d34f87bdf406815196a29d
Source dataset
uspto-grants-1996_10
Patent number
US05569674

Linked notes

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