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

HRID 1764863Notes

Reaction equation

HRID 1764863 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-d66e4130f0c54531be05b9b87aef449d
Source dataset
uspto-grants-2007_06
Patent number
USRE039679E1

Reaction notes

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