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

HRID 2182866Notes

Reaction equation

HRID 2182866 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].S(Cl)([Cl:16])=O>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

To a solution of 3,5-dimethylphenoxyacetic acid (9.0 g, 50 mmole) in benzene (100 mL) was added thionyl chloride (10.89 mL). The resulting mixture was refluxed for 2 hr, then the benzene was removed by distillation. The residual material was dried in vacuo to give 3,5-dimethylphenoxyacetyl chloride, which was dissolved in 20 ml of acetonitrile and used in situ. L-Glutamic acid (8.8 g, 60 mmole) was dissolved in a solution of sodium carbonate (12.72 g, 150 mL, 120 mmole) and the 3,5-dimethylphenoxyacetyl chloride in the acetonitrile solution was slowly added while the pH 8 was adjusted from time-to-time by adding sodium carbonate solution. The reaction mixture was stirred at room temperature for 2 hr, and acidified to pH 2 to give a solid precipitate. The solid precipitate was collected by filtration, treated with hot benzene, filtered, again and washed again with benzene to give Intermediate 31 (9.2 g).

Workup

  1. temperatureThe resulting mixture was refluxed for 2 hr
  2. customthe benzene was removed by distillation
  3. customThe residual material was dried in vacuo

Sources & evidence

ORD record
ord-a91d0d3067154b658caa749dd694328b
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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