Water → 1-(p-Toluenesulfonyloxy)-4-acetoxy-5-(3-trifluoromethylphenoxy)pentane

HRID 1833485Notes

Reaction equation

HRID 1833485 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]([O:15][CH:16]([CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=1)[CH2:17][CH2:18][CH2:19][OH:20])(=[O:14])[CH3:13].O>N1C=CC=CC=1.CCOCC>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:20][CH2:19][CH2:18][CH2:17][CH:16]([O:15][C:12](=[O:14])[CH3:13])[CH2:21][O:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 962Water2×HCID 73974-Toluenesulfonyl chlorideHCID 213175614-Acetoxy-5-(3-trifluoromethylphenoxy)-1-pentanol

Product 1

HCID 213176291-(p-Toluenesulfonyloxy)-4-acetoxy-5-(3-trifluoromethylphenoxy)pentaneYield 94%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of p-toluenesulfonyl chloride (65.2 g., 0.342 mole) in pyridine (130 ml.) is cooled in a cold water (10°-15°) bath while 4-acetoxy-5-(3-trifluoromethylphenoxy)-1-pentanol (90.7 g., 0.297 mole) is added dropwise with stirring during 70 minutes. The mixture is then stirred 2 hours in the same cold water bath. It is poured into 400 ml. of water. The oily product is taken up in ether, washed with water, 2N hydrochloric acid and dilute sodium bicarbonate solution and dried over magnesium sulfate. The solvent is evaporated in vacuo to leave 125 g. (94%) of the crude title compound as a nearly colorless oil.

Workup

  1. additionis added dropwise
  2. additionIt is poured into 400 ml
  3. washwashed with water, 2N hydrochloric acid and dilute sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent is evaporated in vacuo
  6. customto leave 125 g

Sources & evidence

ORD record
ord-17e3abf0e17b444a9bc8c74d4ecc5b2c
Source dataset
uspto-grants-1978_01
Patent number
US04066675

Reaction notes

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