Hydrochloric Acid → Benzeneacetic acid, alpha-ethyl-, methyl ester

HRID 494600

Reaction equation

HRID 494600 reaction equation
[C:1]1([CH:7]([CH2:11][CH3:12])[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:14]O>>[C:1]1([CH:7]([CH2:11][CH3:12])[C:8]([O:10][CH3:14])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 70122-Phenylbutyric Acid

Product 1

HCID 102780Benzeneacetic acid, alpha-ethyl-, methyl ester

Procedure

2-Phenylbutyric acid (10 g, 61 mmole) was dissolved in methanol (30 ml) treated with concentrated HCl (1 ml) and heated at reflux for 20 hours. The heating was stopped and the reaction mixture cooled to room temperature. The solvent was removed in vacuo and the oily residue was treated with ethyl acetate (100 ml). The organic layer was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a clear oil. Yield 10.61 g (97%). 1H NMR (300 MHz, DMSO-d6): δ ppm 0.81 (t, J=7.35 Hz, 3H) 1.69 (m, 1H) 1.98 (m, 1H) 3.53 (d, J=7.35 Hz, 1H) 3.58 (s, 3H) 7.30 (m, 5H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 20 hours
  3. customThe solvent was removed in vacuo
  4. additionthe oily residue was treated with ethyl acetate (100 ml)
  5. washThe organic layer was washed with saturated sodium bicarbonate solution and saturated sodium chloride solution
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-839125d2cbb44722ad98420b53950150
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Linked notes

Loading…