Thionyl Chloride → (3,5-Dimethylphenoxy)acetyl chloride

HRID 2182850Notes

Reaction equation

HRID 2182850 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([CH3:13])[CH:12]=1)[O:5][CH2:6][C:7](O)=[O:8].O=S(Cl)[Cl:16]>C1C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([CH3:13])[CH:12]=1)[O:5][CH2:6][C:7]([Cl:16])=[O:8]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 794053,5-Xylyloxyacetic acid

Product 1

HCID 12761006(3,5-Dimethylphenoxy)acetyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of the 3,5-dimethylphenoxyacetic acid (prepared as described above, 9.3 g, 51.6 mmol) and SOCl2 (11.3 mL, 18.5 g, 156 mmol, 3.0 eq) in 10 mL of benzene was refluxed for 2 h. Then volatile materials were removed by vacuum distillation to give 3,5-dimethylphenoxyacetic acid chloride as a light brown oil. To an ice-bath cooled solution of 6-amino-n-caproic acid (13.5 g, 103 mmol, 2.0 eq) and NaOH (4.2 g, 105 mmol) in 100 mL of H2O and 130 mL of CH3CN were added drop-wise a solution of the acid chloride (prepared in previous step) in 100 mL of CH3CN and a solution of NaHCO3 (6.5 g, 77.0 mmol, 1.5 eq) in 80 mL of H2O. The mixture was stirred vigorously overnight. Then most of the CH3CN was removed under reduced pressure and the mixture was acidified to pH 2 at room temperature with conc-HCl. The resulting white precipitates were collected by filtration, washed with H2O, followed by hexane, and thereafter dried under high vacuum to yield Intermediate 15 (14.5 g, 95%) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-9f42f1f229cf4e2db970ba7e9c696989
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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