Thionyl Chloride → 4-Benzyloxyphenylacetyl Chloride

HRID 569602Notes

Reaction equation

HRID 569602 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:21])=O>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([Cl:21])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 810334-Benzyloxyphenylacetic acid

Product 1

HCID 113574424-Benzyloxyphenylacetyl Chloride

Procedure

In this example, 6.05 g of 4-benzyloxyphenylacetic acid obtained as in Example 1, is dissolved in 125 ml of thionyl chloride, and boiled for 4 hours. Excess thionyl chloride is distilled off under reduced pressure, and the residue is dried, whereby 4-benzyloxyphenylacetic acid chloride is obtained. The thus obtained product is then dissolved in 25 ml of anhydrous benzene, and the resulting solution is added dropwise to 8.3 g of triethyl phosphite in a nitrogen gas stream with stirring under ice cooling.

Workup

  1. distillationExcess thionyl chloride is distilled off under reduced pressure
  2. customthe residue is dried

Sources & evidence

ORD record
ord-e70b1f8ae31b48ab8bd6366ff0d71c65
Source dataset
uspto-grants-1988_03
Patent number
US04733000

Reaction notes

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