Methanol → Methyl 3-(4-chlorophenyl)propanoate

HRID 387512

Reaction equation

HRID 387512 reaction equation
O=S(Cl)Cl.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:8][CH:7]=1.[CH3:17]O>>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 123137beta-(p-Chlorophenyl)propionic acid

Product 1

HCID 8027172Methyl 3-(4-chlorophenyl)propanoateYield 97%

Procedure

Neat SOCl2 (25.7 g, 216.7 mmol) was added dropwise to a −60° C. solution of MeOH (100 mL). Upon completion of the addition, 3-(4-chlorophenyl)propanoic acid (10.0 g, 54.1 mmol) was added in several portions. Upon completion of the addition, the cooling bath was removed, and the reaction mixture was slowly warmed to room temperature and stirred overnight. The reaction was then concentrated to dryness, and the resulting residue was dissolved in DCM (100 mL), washed with saturated NaHCO3, dried (MgSO4), filtered, and concentrated to give methyl 3-(4-chlorophenyl)propanoate as an oil (10.48 g, 97%).

Workup

  1. additionwas added in several portions
  2. additionUpon completion of the addition
  3. customthe cooling bath was removed
  4. concentrationThe reaction was then concentrated to dryness
  5. dissolutionthe resulting residue was dissolved in DCM (100 mL)
  6. washwashed with saturated NaHCO3
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-96fc7ea5608b408f94f6ac57c1dcbf9e
Source dataset
uspto-grants-2013_02
Patent number
US08372842B2

Linked notes

Loading…