Water → 2-(Cyclohexylmethyl)hexyl methanesulfonate

HRID 1248197Notes

Reaction equation

HRID 1248197 reaction equation
[CH:1]1([CH2:7][CH:8]([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:9][OH:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:15][S:16](Cl)(=[O:18])=[O:17].O>N1C=CC=CC=1>[CH3:15][S:16]([O:10][CH2:9][CH:8]([CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH2:11][CH2:12][CH2:13][CH3:14])(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 134765532-(Cyclohexylmethyl)hexan-1-ol

Product 1

HCID 134765542-(Cyclohexylmethyl)hexyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-(cyclohexylmethyl)hexan-1-ol (1.3 g) in 10 ml of dry pyridine under nitrogen was cooled to 0° C. and treated dropwise with stirring with 1.0 g of methanesulfonyl chloride. After 1 hour the mixture was poured into water and extracted with ethyl acetate. The extracts were washed twice with dilute hydrochloric acid, once with brine and dried (MgSO4). Evaporation of the solvent gave an oil, 2-(cyclohexylmethyl)hex-1-yl methanesulfonate, which was used directly in the next step.

Workup

  1. additiontreated dropwise
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed twice with dilute hydrochloric acid, once with brine
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-06a99aeece8747f583305c5554c24698
Source dataset
uspto-grants-1985_06
Patent number
US04522948

Reaction notes

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