4-Toluenesulfonyl chloride → HCID 86751638, compound

HRID 2294698Notes

Reaction equation

HRID 2294698 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[C@H:12]1([CH2:18][OH:19])[CH2:17][CH2:16][CH:15]=[CH:14][CH2:13]1>N1C=CC=CC=1>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:19][CH2:18][C@H:12]2[CH2:17][CH2:16][CH:15]=[CH:14][CH2:13]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 12299191HCID 12299191, compound

Product 1

HCID 86751638HCID 86751638, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of 10.48 g (55 mmol) of p-toluenesulphonyl chloride in 10 ml of pyridine is slowly added dropwise to a solution, cooled to -10°, of 5.6 g (50 mmol) of (S)-3-cyclohexene-1-methanol in 20 ml of pyridine. The solution is stirred at -10° for 64 hours, thereafter evaporated in a high vacuum and the residue is taken up in ether. The ether solution is washed in succession with 1N hydrochloric acid, water and saturated sodium bicarbonate solution and subsequently evaporated under reduced pressure. [(S)-3-Cyclohexen-1-yl]methyl p-toluenesulphonate is thereby obtained as a colourless oil; MS: 173 (M)+.

Workup

  1. customevaporated in a high vacuum
  2. washThe ether solution is washed in succession with 1N hydrochloric acid, water and saturated sodium bicarbonate solution
  3. customsubsequently evaporated under reduced pressure

Sources & evidence

ORD record
ord-9c678e6edf2e4852b50ba426706d8f2e
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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