Methanol → Methyl 4-chlorophenylacetate

HRID 1493234Notes

Reaction equation

HRID 1493234 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>[CH3:19][O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=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

4-Chlorophenylacetic acid (100 g, 0.59 mol) was dissolved in 1,2-dichloroethane (165 ml) and methanol (96 ml, 2.4 moles) and to the solution was added concentrated sulfuric acid (2.75 ml), followed by refluxing for 6 hours. The mixture was cooled and aqueous NaHCO3 was added, followed by stirring. The resulting organic layer was separated, dried over anhydrous sodium sulfate, collected by filtration and concentrated to dryness to obtain methyl-(4-chlorophenyl)-acetate (102 g, yield 94%).

Workup

  1. temperatureby refluxing for 6 hours
  2. temperatureThe mixture was cooled
  3. customThe resulting organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationcollected by filtration
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-3b3347417c4b4e078abe7778c0d9167e
Source dataset
uspto-grants-1991_06
Patent number
US05021435

Reaction notes

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