4-Toluenesulfonyl chloride → HCID 561724, compound

HRID 2374114Notes

Reaction equation

HRID 2374114 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>ClCCl.N1C=CC=CC=1>[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 748286-Chloro-1-hexanol

Product 1

HCID 561724HCID 561724, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 6-chlorohexan-1-ol (25.0 g, 0.183 mol) in dichloromethane (DCM) (166 ml) and pyridine (33 ml) was cooled to −5° C. Toluene-p-sulphonyl chloride (40.1 g, 0.210 mol) was slowly added to the stirred solution and left to react overnight. The reaction mixture was treated with ice (80 g) and left stirring for 1 h. The organic layer was washed with ice cold 2M-sulphuric acid and then dried (MgSO4). The solvent was removed in vacuo and the residue was purified by column chromatography [DCM] to give a white powder 40.20 g, 85%; mp 27-28° C.

Workup

  1. waitleft
  2. customto react overnight
  3. waitleft
  4. washThe organic layer was washed with ice cold 2M-sulphuric acid
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by column chromatography [DCM]

Sources & evidence

ORD record
ord-9937ef5df6384a41b6b90e5d263e746c
Source dataset
uspto-grants-2008_12
Patent number
US07462427B2

Reaction notes

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