1,1'-(4-Chloro-1-butenylidene)bisbenzene → 1,1'-(4-Chlorobutylidene)bisbenzene

HRID 50986Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][CH:4]=[C:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CCOC(C)=O.[Pd]>[Cl:1][CH2:2][CH2:3][CH2:4][CH:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 4-chloro-1,1-diphenyl-1-butene (200 mg, 0.82 mmol) in EtOAc (8.0 mL) was added Pd/C (10%, 50 mg). The reaction mixture was stirred under H2 atmosphere for 15 h at 20° C. The reaction mixture was filtered through celite and the filterate was concentrated to give the analytically pure 4-Chloro-1,1-diphenylbutane (201 mg, 99%) as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ1.70-1.81 (m, 2H), 2.16-2.25 (m, 2H), 3.54 (t, 2H, J=6.5 Hz), 3.91 (t, 1H, J=7.8 Hz), 7.15-7.31 (m, 10H) ppm.

Workup

filtrationThe reaction mixture was filtered through celite
concentrationthe filterate was concentrated

Sources & evidence

ORD record: ord-417c6a89f36b4fb7b70b9c4fc2c913d4
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713471B1

Reaction notes

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