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

HRID 1194642Notes

Reaction equation

HRID 1194642 reaction equation
[S:1]([Cl:4])([Cl:3])=[O:2].[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([OH:27])=O)=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>>[S:1]([Cl:4])([Cl:3])=[O:2].[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([Cl:3])=[O:27])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 147447934'-(Benzyloxy)[1,1'-biphenyl]-4-carboxylic acid

Product 2

HCID 24386Thionyl ChlorideHCID 150849044'-(Phenylmethoxy)(1,1'-biphenyl)-4-carbonyl chlorideYield 154.9%

Procedure

Thionyl chloride (140 g, 1.18 mol) was added to 4'-benzyloxybiphenyl-4-carboxylic acid (300 g, 0.98 mol), followed by refluxing the mixture for about 2 hours, thereafter removing excess thionyl chloride under reduced pressure to obtain 4'-benzyloxybiphenyl-4-carboxylic chloride (295 g).

Workup

  1. temperatureby refluxing the mixture for about 2 hours

Sources & evidence

ORD record
ord-c56cee0c4f334acc92c8cd65080e1f34
Source dataset
uspto-grants-1989_03
Patent number
US04816181

Reaction notes

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