Hydrochloric Acid → Ethyl phenyllactate, (+-)-

HRID 1359201Notes

Reaction equation

HRID 1359201 reaction equation
[OH:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([OH:5])=[O:4].Cl.O.C(=O)([O-])O.[Na+].[CH2:20](O)[CH3:21]>>[OH:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([O:5][CH2:20][CH3:21])=[O:4]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 3848(+-)-3-Phenyllactic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 6429708Ethyl phenyllactate, (+-)-Yield 82%

Procedure

A solution of 2-hydroxy-3-phenylpropanoic acid (2.10 g, 12.6 mmol) in ethanol (50 mL) was saturated with gaseous hydrochloric acid and allowed to stand at room temperature overnight. The reaction mixture was poured into water, neutralized with solid sodium hydrogen carbonate and extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to give ethyl 2-hydroxy-3-phenylpropanoate as a peach-colored oil (2.00 g, 82%); 1HNMR (200 MHz, DMSO-d6): δ7.15-7.35 (m, 5H), 5.4-5.6 (br, 1H), 4.15-4.3 (br, 1H), 4.05 (q, 2H, J=7.3 Hz), 2.75-3.0 (m, 2H), and 1.2 ppm (t, 3H, J=7.4 Hz).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c86034687ad043ab94958570dbcfd095
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

Loading…