Water → 1,1'-(2,2-Dichlorocyclopropane-1,1-diyl)bis(4-methoxybenzene)

HRID 1657974Notes

Reaction equation

HRID 1657974 reaction equation
[CH:1]([Cl:4])(Cl)[Cl:2].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH2:14])=[CH:9][CH:8]=1.CC(C)([O-])C.[K+].O>CC1CCCCC1>[CH3:22][O:21][C:18]1[CH:17]=[CH:16][C:15]([C:13]2([C:10]3[CH:9]=[CH:8][C:7]([O:6][CH3:5])=[CH:12][CH:11]=3)[CH2:14][C:1]2([Cl:4])[Cl:2])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 3167241,1-bis(4-methoxyphenyl)ethyleneHCID 23665647Potassium tert-butoxide

Product 1

HCID 135803511,1'-(2,2-Dichlorocyclopropane-1,1-diyl)bis(4-methoxybenzene)

Reagents, catalysts & solvents 1

HCID 7962MethylcyclohexaneSolvent

Conditions

Temperature
20 °C

Procedure

Chloroform (0.2 moles) was added dropwise with stirring to a solution of 1,1-di-(p-methoxyphenyl)ethylene (0.1 mole) in methyl cyclohexane containing potassium tert-butoxide (0.4 moles) at 0°C. The mixture was allowed to warm to 20°C. overnight and then poured into water. The oil phase was separated and the solvent recovered. The residual solid was recrystallized from petroleum ether to give 1-(p-methoxyphenyl)-1-(p-methoxyphenyl)-2,2-dichlorocyclopropane, m.p. 141°C.

Workup

  1. customThe oil phase was separated
  2. customthe solvent recovered
  3. customThe residual solid was recrystallized from petroleum ether

Sources & evidence

ORD record
ord-be0f03a9f532479d9f0063fdb28dbe81
Source dataset
uspto-grants-1976_06
Patent number
US03962356

Reaction notes

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