4-Toluenesulfonyl chloride → 11-Phenyl-8-undecenol tosylate

HRID 978675Notes

Reaction equation

HRID 978675 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:12]1([CH2:18][CH2:19][CH:20]=[CH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>N1C=CC=CC=1>[S:7]([O:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH:21]=[CH:20][CH2:19][CH2:18][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 5394137611-Phenyl-8-undecenol

Product 1

HCID 5396673911-Phenyl-8-undecenol tosylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Toluenesulphonyl chloride (1.3 g) was added in portions to a stirred solution of the product of step (c) (1.5 g) in pyridine at 0°-5° C. The mixture was stirred for 16 hours at 0°-5° C. then poured onto ice-hydrochloric acid and extracted with ether. The extract was washed with sodium bicarbonate and sodium chloride solutions, dried and evaporated to give the title compound as a pale oil.

Workup

  1. additionthen poured onto ice-hydrochloric acid
  2. extractionextracted with ether
  3. washThe extract was washed with sodium bicarbonate and sodium chloride solutions
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-891f52ea84ee454fa86c9e9caab3951c
Source dataset
uspto-grants-1987_05
Patent number
US04665189

Reaction notes

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