Methanesulfonyl chloride → HCID 20540205, compound

HRID 1065272Notes

Reaction equation

HRID 1065272 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>N1C=CC=CC=1>[CH3:16][S:17]([O:15][CH:12]1[CH2:13][CH2:14][CH:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH2:10][CH2:11]1)(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 186058474-(4-Methoxyphenyl)cyclohexanol

Product 1

HCID 20540205HCID 20540205, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
65 °C

Procedure

To a stirred mixture of 75 parts of 4-(4-methoxyphenyl)cyclohexanol and 1000 parts of pyridine are added dropwise 62 parts of methanesulfonyl chloride (exothermic reaction: temperature rises to 40° C.). Upon completion, the whole is heated to 65° C. and stirring is continued for 2 hours, while meantime the mixture is allowed to cool to room temperature. The reaction mixture is evaporated and 1000 parts of water are added to the residue. The product is extracted with dichloromethane. The extract is washed with water, dried, filtered and evaporated. The residue is crystallized from 2-propanol, yielding 80.5 parts of 4-(4-methoxyphenyl)cyclohexyl methanesulfonate.

Workup

  1. temperatureto cool to room temperature
  2. customThe reaction mixture is evaporated
  3. addition1000 parts of water are added to the residue
  4. extractionThe product is extracted with dichloromethane
  5. washThe extract is washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is crystallized from 2-propanol

Sources & evidence

ORD record
ord-1412152de146454ea222f23e82dd80ad
Source dataset
uspto-grants-1982_05
Patent number
US04329353

Reaction notes

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