Cyclohexylbenzene → 4-Cyclohexylbenzene-1-sulfonyl chloride

HRID 619074

Reaction equation

HRID 619074 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:13][S:14](O)(=[O:16])=[O:15].[Cl-].[NH4+]>C(Cl)Cl>[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([S:14]([Cl:13])(=[O:16])=[O:15])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 13229CyclohexylbenzeneHCID 24638Chlorosulfonic acidHCID 25517Ammonium Chloride

Product 1

HCID 43394424-Cyclohexylbenzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 10.6 ml of phenylcyclohexane in 100 ml of methylene chloride was added at 5° C. within 30 minutes to 13.8 ml of chlorosulfonic acid. The mixture was stirred at 5° C. for 1 hour, poured into 400 ml of a 20% ammonium chloride solution and extracted twice with 300 ml of methylene chloride each time. The organic phases were combined, dried with magnesium sulphate and the solvent was removed on a rotary evaporator. 13.6 g of 4-cyclohexyl-benzenesulfonyl chloride separated as a reddish oil, which was used without further purification.

Workup

  1. extractionextracted twice with 300 ml of methylene chloride each time
  2. dry with materialdried with magnesium sulphate
  3. customthe solvent was removed on a rotary evaporator
  4. custom13.6 g of 4-cyclohexyl-benzenesulfonyl chloride separated as a reddish oil, which
  5. customwas used without further purification

Sources & evidence

ORD record
ord-fe06b79832ba4211b5f8354192793c54
Source dataset
uspto-grants-1999_09
Patent number
US05958910

Linked notes

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