Thionyl Chloride → HCID 54264694, compound

HRID 867360Notes

Reaction equation

HRID 867360 reaction equation
[CH2:1]([O:9][C:10]1[CH:11]=[C:12]([C:22]([OH:24])=O)[C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].S(Cl)([Cl:27])=O>>[CH2:1]([O:9][C:10]1[CH:11]=[C:12]([C:22]([Cl:27])=[O:24])[C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 23162226HCID 23162226, compound

Product 1

HCID 54264694HCID 54264694, compound

Procedure

40 ml of thionyl chloride was added to 5.0 g of 4-octyloxybiphenylcarboxylic acid and the mixture was refluxed under heat for 3 hours. Excess of thionyl chloride was distilled off to obtain 4-octyloxybiphenylcarboxylic acid chloride, which was then added to a solution of 5.0 g of hydroquinone in 50 ml of pyridine. After 2 hours of reaction, the mixture was refluxed under heat for 10 hours, charged into ice water, and extracted with benzene. The extract was purified with a silica gel column chromatography to obtain 4-hydroxyphenyl estcr of 4-octyloxybiphenylcarboxylic acid.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heat for 3 hours
  3. distillationExcess of thionyl chloride was distilled off

Sources & evidence

ORD record
ord-8f3ab8d53e4a4089bd7fcfef94517d48
Source dataset
uspto-grants-1988_10
Patent number
US04775223

Reaction notes

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