Chloroacetic Acid → [3-(Propan-2-yl)phenoxy]acetyl chloride

HRID 2182858Notes

Reaction equation

HRID 2182858 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[O:7][CH2:8][C:9](O)=[O:10])([CH3:3])[CH3:2].C(C1C=C(O)C=CC=1)(C)C.[Cl:25]CC(O)=O.[OH-].[Na+].O=S(Cl)Cl>C1C=CC=CC=1>[CH:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[O:7][CH2:8][C:9]([Cl:25])=[O:10])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 300Chloroacetic AcidHCID 120593-IsopropylphenolHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 14054421[3-(Propan-2-yl)phenoxy]acetic acid

Product 1

HCID 20786371[3-(Propan-2-yl)phenoxy]acetyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 3-isopropylphenoxyacetic acid (prepared by the reaction of 3-isopropylphenol with chloroacetic acid in the presence of sodium hydroxide, 5.0 g, 25.8 mmol) and SOCl2 (5.0 mL, 8.2 g, 68.8 mmol) in 10 mL of benzene was refluxed for 2 h. Thereafter volatile materials were removed by vacuum distillation to give 3-isopropylphenoxyacetic acid chloride as a light brown oil. To an ice-bath cooled solution of 4-aminobutyric acid (5.3 g, 51.6 mmol, 2.0 eq) and NaOH (2.0 g, 51.6 mmol) in 60 mL of H2O and 80 mL of CH3CN were added drop-wise the acid chloride in 40 mL of CH3CN and NaHCO3 (3.3 g, 38.7 mmol, 1.5 eq) in 50 mL of H2O. The resulting mixture was stirred vigorously for 5 h.

Workup

  1. temperaturewas refluxed for 2 h
  2. customThereafter volatile materials were removed by vacuum distillation

Sources & evidence

ORD record
ord-f3ec01d545c64f89ae43b70ec7fa27e7
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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