Octane → 7,7-Dichlorobicyclo[4.1.0]heptane

HRID 436352Notes

Reaction equation

HRID 436352 reaction equation
[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[CH:7](Cl)([Cl:9])[Cl:8].[OH-].[Na+].CCCCCCCC>ClCCl>[Cl:8][C:7]1([Cl:9])[CH:6]2[CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]2

Participants

6

Reactant 4

HCID 356OctaneHCID 6212ChloroformHCID 8079CyclohexeneHCID 14798Sodium Hydroxide

Product 1

HCID 2443757,7-Dichlorobicyclo[4.1.0]heptane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

In a flask provided with a one-blade paddle mixer, a mixture of 1.64 grams of cyclohexene, 23.7 grams of chloroform, 20 milliliters of 50%w aqueous sodium hydroxide, 5 milliliters of dichloromethane, 1 milliliter of n-octane (to serve as a GLC marker) and 0.010 gram of the catalyst indicated in Table I was stirred vigorously at 40° C. Samples were taken after stirring had been started at the times indicated in Table I. Table I presents the yields of 7,7-dichloronorcarane. The selectivity to the latter compound was 100% in all cases. A dash indicates that no analysis was effected.

Workup

  1. customIn a flask provided with a one-blade paddle mixer
  2. stirringafter stirring

Sources & evidence

ORD record
ord-6407c207b1a84306a483950c584c36f2
Source dataset
uspto-grants-1977_02
Patent number
US04008287

Reaction notes

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