Dichloromethane → 1-Methanesulfonyloxy-2-allylcyclohexane

HRID 128316Notes

Reaction equation

HRID 128316 reaction equation
ClCCl.[CH2:4]([CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[OH:13])[CH:5]=[CH2:6].[CH3:14][S:15](Cl)(=[O:17])=[O:16]>C(N(CC)CC)C>[CH3:14][S:15]([O:13][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][CH:7]1[CH2:4][CH:5]=[CH2:6])(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 117892912-(Prop-2-en-1-yl)cyclohexan-1-ol

Product 1

HCID 204988971-Methanesulfonyloxy-2-allylcyclohexane

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 250 ml. of dichloromethane, 25 g. 2-allylcyclohexanol and 16.7 g. of triethylamine cooled in an ice-salt bath to -10° C. is added dropwise, over 15 minutes, 18.9 g. of methanesulfonyl chloride. The mixture is cooled at -10° C. to -15° C. for 30 minutes and then washed with 300 ml. each of cold water, 10% hydrochloric acid, sodium carbonate solution and with saturated sodium chloride solution. The organic layer is dried with magnesium sulfate and concentrated in vacuo to give a pale yellow oil.

Workup

  1. additionTo a mixture of 250 ml
  2. additionis added dropwise, over 15 minutes
  3. temperatureThe mixture is cooled at -10° C. to -15° C. for 30 minutes
  4. washwashed with 300 ml
  5. dry with materialThe organic layer is dried with magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a pale yellow oil

Sources & evidence

ORD record
ord-79adca8ca5ed4c6e96fea4c8719e822b
Source dataset
uspto-grants-1981_03
Patent number
US04259352

Reaction notes

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