4-Toluenesulfonyl chloride → O-(p-Toluenesulfonyl)-3-(4-Fluorophenoxy)propanol

HRID 619689Notes

Reaction equation

HRID 619689 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>N1C=CC=CC=1>[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19]([O:10][CH2:9][CH2:8][CH2:7][O:6][C:5]2[CH:11]=[CH:12][C:2]([F:1])=[CH:3][CH:4]=2)(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 136912113-(4-Fluorophenoxy)propan-1-ol

Product 1

HCID 15858753O-(p-Toluenesulfonyl)-3-(4-Fluorophenoxy)propanolYield 93%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
5 °C

Procedure

3-(4-Fluorophenoxy)propanol (7.55 g, 44 mmol) was stirred in 50 mL of pyridine under a nitrogen atmosphere at 5° C. p-Toluenesulfonyl chloride (9.2 g, 50 mmol) was added in one portion and the resulting solution was allowed to stir at 5° C. for 1 hour and then was placed in a refrigerator set at 5° C. overnight. The reaction was then poured into about 300 mL of ice water. This mixture was extracted three times with diethyl ether. The combined extracts were washed 2 times with cold 1N hydrochloric acid and once with cold water. The extracts were then dried over sodium sulfate/potassium carbonate, filtered, and concentrated to give 13.24 g of a solid product. Yield: 93%.

Workup

  1. additionwas added in one portion
  2. waitset at 5° C. overnight
  3. extractionThis mixture was extracted three times with diethyl ether
  4. washThe combined extracts were washed 2 times with cold 1N hydrochloric acid
  5. dry with materialThe extracts were then dried over sodium sulfate/potassium carbonate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4e6bcd6f904b49d6b30dd9c33e740023
Source dataset
uspto-grants-1999_09
Patent number
US05959121

Reaction notes

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