Methanol → Methyl 4-chlorophenylacetate

HRID 231827Notes

Reaction equation

HRID 231827 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.CO.S(=O)(=O)(O)O.[C:19](=O)(O)[O-].[Na+]>ClCCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:19])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 15880(4-Chlorophenyl)acetic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 104196Methyl 4-chlorophenylacetateYield 94%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 100 g (0.59 mole) of 4-chlorophenylacetic acid in 165 ml of 1,2-dichloroethane and 96 ml (2.4 moles) of methanol was added 2.75 ml of concentrated sulfuric acid, and the mixture was refluxed for 6 hours. It was then cooled, poured into an aqueous sodium bicarbonate solution and stirred. The organic layer was separated, dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated to dryness to give 102 g (94% yield) of methyl (4-chlorophenyl)acetate.

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. temperatureIt was then cooled
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-992bde8253b34d2fab6e02c61c6ecedd
Source dataset
uspto-grants-1989_07
Patent number
US04849434

Reaction notes

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