Thionyl Chloride → 1,1'-(4-Chloro-1-butenylidene)bisbenzene

HRID 542438Notes

Reaction equation

HRID 542438 reaction equation
S(Cl)([Cl:3])=O.[CH:5]1([C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)O)[CH2:7][CH2:6]1>>[Cl:3][CH2:7][CH2:6][CH:5]=[C:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 79850alpha-Cyclopropyl-alpha-phenylbenzenemethanol

Product 1

HCID 798211,1'-(4-Chloro-1-butenylidene)bisbenzene

Procedure

Thionyl chloride (8.9 ml) is added slowly to cyclopropyldiphenylcarbinol (25 g) and the mixture is stirred until gas evolution ceases. Vacuum distillation affords 4-chloro-1,1-diphenylbutene. Conversion of the chloride to the cyanide is accomplished using the method of R. A. Smiley and C. Arnold, J. Org. Chem. 1960, 25, 257. The resulting nitrile (14.72 g) is reduced with Raney-Cobalt (4 g) in tetrahydrofuran (150 ml) and triethylamine (4 ml) at 15°-130° C. and 1450-2100 PSIG. The olefinic moiety is then reduced at room temperature in methanol (150 ml) with concentrated sulfuric acid (3.5 ml) and 20% Pd-C (5 g, added portionwise during the course of the reaction) at room temperature and 50 PSIG hydrogen.

Workup

  1. distillationVacuum distillation

Sources & evidence

ORD record
ord-f4e2034f8039496599878b3c9983db43
Source dataset
uspto-grants-1987_04
Patent number
US04657897

Reaction notes

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