Methanesulfonyl chloride → HCID 13655348, compound

HRID 745277Notes

Reaction equation

HRID 745277 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:10][OH:11].[CH3:19][S:20](Cl)(=[O:22])=[O:21]>N1C=CC=CC=1>[CH3:19][S:20]([O:11][CH2:10][CH:9]([C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])[CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)(=[O:22])=[O:21]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 13655347HCID 13655347, compound

Product 1

HCID 13655348HCID 13655348, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred and cooled (ice-bath) mixture of 22 parts of 2,4-dichloro-β-(cyclohexylmethyl)benzeneethanol and 50 parts of pyridine are added dropwise 8.8 parts of methanesulfonyl chloride. Upon completion, stirring is continued for 3 hours at room temperature. The reaction mixture is poured onto water and the product is extracted twice with trichloromethane. The combined extracts are washed twice with a diluted hydrochloric acid solution and once with water, dried, filtered and evaporated. The residue is crystallized from 2,2'-oxybispropane, yielding 16.5 parts of 3-cyclohexyl-2-(2,4-dichlorophenyl)propyl methanesulfonate; mp. 105.1° C.

Workup

  1. temperaturecooled
  2. stirringUpon completion, stirring
  3. additionThe reaction mixture is poured onto water
  4. extractionthe product is extracted twice with trichloromethane
  5. washThe combined extracts are washed twice with a diluted hydrochloric acid solution and once with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is crystallized from 2,2'-oxybispropane

Sources & evidence

ORD record
ord-b57e9eeabebb423aac11900eb6ad1fef
Source dataset
uspto-grants-1986_07
Patent number
US04598085

Reaction notes

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