4-Toluenesulfonyl chloride → 11-Phenylundecanol tosylate

HRID 978677Notes

Reaction equation

HRID 978677 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][CH2:20][CH2:21][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][CH2:21][CH2:20][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 11651716Benzeneundecanol

Product 1

HCID 5393925311-Phenylundecanol tosylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Toluenesulphonyl chloride (2.6 g) was added in portions to a stirred solution of the product of step (a) (2.9 g) in pyridine (10 ml) at 0° C. The solution 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. The residue was chromatographed on silica gel eluting with 1:1 dichloromethane:hexane to give the title compound as a colourless 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
  6. customThe residue was chromatographed on silica gel eluting with 1:1 dichloromethane

Sources & evidence

ORD record
ord-c6796cba41954d6eb4b6efc77229340b
Source dataset
uspto-grants-1987_05
Patent number
US04665189

Reaction notes

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