Methanol → Benzeneacetic acid, alpha-ethyl-, methyl ester

HRID 247456

Reaction equation

HRID 247456 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.S(Cl)(Cl)=O.[CH3:17]O>C(OCC)C>[C:1]1([CH:7]([CH2:11][CH3:12])[C:8]([O:10][CH3:17])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 70122-Phenylbutyric AcidHCID 24386Thionyl Chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 102 g. of 2-phenylbutyric acid dissolved in 1 liter of methanol was added 2 ml of thionyl chloride. The solution was allowed to stand at room temperature overnight. The solvent was removed in vacuo to yield an oil which was dissolved in diethyl ether, washed successively with dilute sodium bicarbonate solution and saturated sodium chloride solution, dried over anhydrous potassium carbonate, and concentrated in vacuo. Distillation yielded 101 g of the title compound as a water-white oil, b.p. 62°-65°/0.5 mm, having the following elemental analysis:

Workup

  1. customThe solvent was removed in vacuo
  2. customto yield an oil which
  3. washwashed successively with dilute sodium bicarbonate solution and saturated sodium chloride solution
  4. dry with materialdried over anhydrous potassium carbonate
  5. concentrationconcentrated in vacuo
  6. distillationDistillation

Sources & evidence

ORD record
ord-6cb8aa009e3d4806be2a7f4eb9928fba
Source dataset
uspto-grants-1987_11
Patent number
US04707499

Linked notes

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