Hydrochloric Acid → 1,1'-(4-Chloro-1-butenylidene)bisbenzene

HRID 50987Notes

Reaction equation

HRID 50987 reaction equation
[CH:1]1([C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)O)[CH2:3][CH2:2]1.[ClH:18]>CC(O)C.CCOCC>[Cl:18][CH2:3][CH2:2][CH:1]=[C:4]([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

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 79850alpha-Cyclopropyl-alpha-phenylbenzenemethanol

Product 1

HCID 798211,1'-(4-Chloro-1-butenylidene)bisbenzeneYield 93%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

Cyclopropyldiphenylmethanol (500 mg, 2.23 mmol) was dissolved in 1M HCl in i-PrOH (4.0 mL). The reaction mixture was then heated at 60° C. for 1 h. The reaction was cooled 20° C. and diluted with Et2O (100 mL). The organic solution was successively washed with H2O, NaHCO3 saturated aqueous solution and brine. It was then dried over MgSO4, filtered, concentrated in vacuo and chromatographed on a silica gel column by elution with Hexanes to give 4-Chloro-1,1-diphenyl-1-butene (506 mg, 93%) as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ2.59 (q, 2H, J=6.9 Hz), 3.58 (t, 2H, J=6.9 Hz), 6.12 (t, 1H, J=7.3 Hz), 7.16-7.42 (m, 10H) ppm.

Workup

  1. temperatureThe reaction was cooled 20° C.
  2. washThe organic solution was successively washed with H2O, NaHCO3 saturated aqueous solution and brine
  3. dry with materialIt was then dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customchromatographed on a silica gel column by elution with Hexanes

Sources & evidence

ORD record
ord-9f18181de81d4a7f961e287e5b077b49
Source dataset
uspto-grants-2004_03
Patent number
US06713471B1

Reaction notes

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