Ethanol → Acetic acid, (4-chlorophenoxy)-, ethyl ester

HRID 895386Notes

Reaction equation

HRID 895386 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH2:18](O)[CH3:19]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]([O:10][CH2:18][CH3:19])=[O:9])=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 26229(4-Chlorophenoxy)acetic acid

Product 1

HCID 26689Acetic acid, (4-chlorophenoxy)-, ethyl esterYield 93%

Procedure

A solution of 4-chlorophenoxyacetic acid (Aldrich) (18.62 g, 99.8 mmoles) and concentrated sulfuric acid (Fisher) (2.5 mL) in ethanol (170 mL) was refluxed with stirring under a DRIERITE tube for 96 hours. The reaction solution was cooled in an ice-bath, and the volatiles were removed by spin evaporation in vacuo to a volume of about 100 mL. The liquid was dissolved in dichloromethane (225 mL) and washed with a solution of 5% aqueous sodium bicarbonate (4×100 mL) and finally with brine (1×50 mL). The solution was dried over sodium sulfate and spin evaporated in vacuo to give 19.97 g (93% yield) of ethyl 4-chlorophenoxyacetate as an amber liquid.

Workup

  1. temperatureThe reaction solution was cooled in an ice-bath
  2. customthe volatiles were removed by spin evaporation in vacuo to a volume of about 100 mL
  3. dissolutionThe liquid was dissolved in dichloromethane (225 mL)
  4. washwashed with a solution of 5% aqueous sodium bicarbonate (4×100 mL) and finally with brine (1×50 mL)
  5. dry with materialThe solution was dried over sodium sulfate
  6. customspin evaporated in vacuo

Sources & evidence

ORD record
ord-b38b2a102af94dd4a65bbda139dfb37a
Source dataset
uspto-grants-2005_07
Patent number
US06916820B1

Reaction notes

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