Thionyl Chloride → 4'-(Phenylmethoxy)(1,1'-biphenyl)-4-carbonyl chloride

HRID 1074302Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([O-:23])=O)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:26])=O>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([Cl:26])=[O:23])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 221564064'-Benzyloxybiphenyl-4-carboxylate

Product 1

HCID 150849044'-(Phenylmethoxy)(1,1'-biphenyl)-4-carbonyl chloride

Procedure

Methyl-4.-hydroxybiphenyl is reacted with benzyl bromide to obtain 4'-benzyloxybiphenyl-4-carboxylate, which is converted through hydrolysis to 4'-benzyloxybiphenyl-4-carboxylate, which is then reacted with thionyl chloride to obtain 4'-benzyloxybiphenyl-4-carboxylic acid chloride. The chloride is reacted with optically active 1-trifluoro-2-octanol 1-trifluoromethylheptyl-4'-benzyloxybiphenyl-4-carboxylate, which is subjected to catalytical hydrogenolysis to obtain 1-trifluoroheptyl-4'-hydroxybiphenyl-4-carboxylate (III).

Sources & evidence

ORD record: ord-cfbae2017bff4714880e6180e9a00ee4
Source dataset: uspto-grants-1990_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04973738

Reaction notes

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