Ethanol → Ethyl 3,4-dichlorophenylacetate

HRID 1860156

Reaction equation

HRID 1860156 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].S(=O)(=O)(O)O.[CH2:18](O)[CH3:19]>>[CH2:18]([O:11][C:10](=[O:12])[CH2:9][C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[CH3:19]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 798743,4-Dichlorophenylacetic acid

Product 1

HCID 2737422Ethyl 3,4-dichlorophenylacetateYield 82.5%

Procedure

A solution of (3,4-dichloro-phenyl)-acetic acid (10.0 g, 0.048 mol) in ethanol (50 mL) was treated with a catalytic amount of sulfuric acid. The reaction mixture was refluxed for 7 h. The reaction was concentrated in vacuo, diluted with diethyl ether, and poured into water. The ether layer was washed with a saturated aqueous sodium bicarbonate solution and water. The organics were then dried over sodium sulfate, filtered, and concentrated in vacuo. Vacuum distillation (bath temperature: 175° C.; head temperature: 125° C.) afforded (3,4-dichloro-phenyl)-acetic acid ethyl ester (9.38 g, 82.5%) as a clear oil: EI-HRMS m/e calcd for C10H10Cl2O2 (M+) 232.0058, found 232.0066.

Workup

  1. temperatureThe reaction mixture was refluxed for 7 h
  2. concentrationThe reaction was concentrated in vacuo
  3. additiondiluted with diethyl ether
  4. additionpoured into water
  5. washThe ether layer was washed with a saturated aqueous sodium bicarbonate solution and water
  6. dry with materialThe organics were then dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. distillationVacuum distillation (bath temperature: 175° C.; head temperature: 125° C.)

Sources & evidence

ORD record
ord-65ffea5f22d74b8181f96cbe5c9fbb5f
Source dataset
uspto-grants-2003_03
Patent number
US06528543B1

Linked notes

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