Water → HCID 14388355, compound

HRID 1885121Notes

Reaction equation

HRID 1885121 reaction equation
[CH2:1]([O:6][CH:7]([CH3:12])[CH2:8][CH2:9][CH2:10][OH:11])[CH2:2][CH2:3][CH2:4][CH3:5].[S:13](Cl)([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14].O>N1C=CC=CC=1>[C:19]1([CH3:20])[CH:21]=[CH:22][C:16]([S:13]([O:11][CH2:10][CH2:9][CH2:8][CH:7]([O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH3:12])(=[O:15])=[O:14])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 14388354HCID 14388354, compound

Product 1

HCID 14388355HCID 14388355, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

17 g of 4-pentyloxypentanol was dissolved in 60 ml of pyridine, and under stirring, 22.4 g of tosyl chloride was added at below 10° C. in 40 min. The mixture was raised to 25° C. and stirred for 3 hours. After the reaction, cold water was added, and the product was extracted with ether, followed by successive washing with 5% hydrochloric acid and water and drying with anhydrous MgSO4. The solvent was distilled off to obtain 31.9 g of 4-pentyloxypentyl p-toluenesulfonate.

Workup

  1. stirringstirred for 3 hours
  2. additionwas added
  3. extractionthe product was extracted with ether
  4. washby successive washing with 5% hydrochloric acid and water
  5. dry with materialdrying with anhydrous MgSO4
  6. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-9328eb988ab84c9e963d0df130832760
Source dataset
uspto-grants-1992_09
Patent number
US05143643

Reaction notes

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