Methanol → Methyl 2-(3,4-dichlorophenyl)acetate

HRID 239212Notes

Reaction equation

HRID 239212 reaction equation
[CH3:1]O.[Cl:3][C:4]1[CH:5]=[C:6]([CH2:11][C:12]([OH:14])=[O:13])[CH:7]=[CH:8][C:9]=1[Cl:10].S(=O)(=O)(O)O>ClCCCl>[Cl:3][C:4]1[CH:5]=[C:6]([CH2:11][C:12]([O:14][CH3:1])=[O:13])[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 798743,4-Dichlorophenylacetic acid

Product 1

HCID 1268257Methyl 2-(3,4-dichlorophenyl)acetateYield 98%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

Methanol (59 mL, 3.0 equivalent amounts) was added to a 1,2-dichloroethane (400 mL) solution of 2-(3,4-dichlorophenyl) acetic acid (100 g, 0.488 mol). The solution was heated to 50° C., and then concentrated sulfuric acid (10 mL) was dropwise added over a period of 15 minutes, followed by stirring at 50° C. for 1.5 hours. The reaction solution was cooled to room temperature, followed by liquid separation to remove a sulfuric acid layer, and the obtained organic layer was sequentially washed with water, a saturated sodium hydrogencarbonate aqueous solution and a saturated salt solution, and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the solvent was distilled off to give the desired product as a colorless oil (105 g, yield: 98%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. customfollowed by liquid separation
  3. customto remove a sulfuric acid layer
  4. washthe obtained organic layer was sequentially washed with water
  5. dry with materiala saturated sodium hydrogencarbonate aqueous solution and a saturated salt solution, and dried over anhydrous magnesium sulfate
  6. customThe drying agent was removed by filtration
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-52139c1006764dfab4279f2c7aa70d45
Source dataset
uspto-grants-2014_02
Patent number
US08642786B2

Reaction notes

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