Thionyl Chloride → 4'-Decyloxybiphenyl-4-carboxylic acid chloride

HRID 579930

Reaction equation

HRID 579930 reaction equation
[CH2:1]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([OH:26])=O)=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].S(Cl)([Cl:29])=O>>[CH2:1]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([Cl:29])=[O:26])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

3

Reactant 2

HCID 24386Thionyl Chloride2×HCID 114510854'-Decyloxybiphenyl-4-carboxylic Acid

Product 1

HCID 140699444'-Decyloxybiphenyl-4-carboxylic acid chloride

Procedure

This ester was dissolved in 50 ml of a 10% by weight solution of sodium hydroxide in a methanol/water mixed solvent (1/1 volume ratio). The solution was refluxed for 6 hours and, subsequently, the reaction mixture was dropped in an ice-cooled aqueous hydrochloric acid solution to form a white powdery precipitate. The precipitate was recovered by filtration, washed with water and then dried to obtain 2.0 g of 4-n-decyloxybiphenyl-4'-carboxylic acid. 2.0 g of the 4-n-decyloxybiphenyl-4'-carboxylic acid was incorporated with 10 ml of thionyl chloride, and the mixture was refluxed for 2 hours. Unreacted thionyl chloride was removed under a reduced pressure to obtain 2.2 g of 4-n-decyloxybiphenyl-4'-carboxylic acid chloride.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. customwas removed under a reduced pressure

Sources & evidence

ORD record
ord-f41d8be85a594289beb00cfa070e48b7
Source dataset
uspto-grants-1988_06
Patent number
US04751018

Linked notes

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