1,1-Dichloroethane → 1-Chloro-1-methyl-2,2-diphenylcyclopropane

HRID 1247703Notes

Reaction equation

HRID 1247703 reaction equation
Cl[CH:2]([Cl:4])[CH3:3].[C:5]1([CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]=[CH:9][CH:8]=[CH:7]C=1.[CH2:19]([Li])CCC.CCCCCC>O.C(OCC)C>[Cl:4][C:2]1([CH3:19])[CH2:3][C:12]1([C:11]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:5]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 63651,1-DichloroethaneHCID 8058HexaneHCID 11502StilbeneHCID 178418339Butyllithium

Product 1

HCID 128696081-Chloro-1-methyl-2,2-diphenylcyclopropaneYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
-40 °C

Procedure

Under a nitrogen atmosphere, 1,1-dichloroethane (30.0 g, 303 mmol), diphenylethylene (5.59 g, 31.0 mmol) and diethyl ether (62 ml) were placed in a reaction flask and cooled to −40° C. To the mixture, n-butyllithium in hexane (45 ml, 1.56M, 70.2 mmol) was added gradually and the mixture was stirred at the same temperature for one hour, followed by warming to room temperature. Then, water was added to the reaction mixture and the organic layer was extracted with toluene. The toluene extract was dried over anhydrous magnesium sulfate and then the solvent was removed under reduced pressure. The concentrate was recrystallized from ethanol to give the title compound (5.91 g, 78%) as white crystal.

Workup

  1. temperatureby warming to room temperature
  2. extractionthe organic layer was extracted with toluene
  3. extractionThe toluene extract
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe concentrate was recrystallized from ethanol

Sources & evidence

ORD record
ord-b0bfc69739404093b84d5e3d93a8775d
Source dataset
uspto-grants-2006_10
Patent number
US07129367B2

Reaction notes

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