4-Toluenesulfonyl chloride → HCID 561724, compound

HRID 1981562Notes

Reaction equation

HRID 1981562 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>N1C=CC=CC=1>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][S:15]([C:12]1[CH:13]=[CH:14][C:9]([CH3:19])=[CH:10][CH:11]=1)(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 748286-Chloro-1-hexanol

Product 1

HCID 561724HCID 561724, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
10 °C

Procedure

A solution of 6-chloro-1-hexanol (100 g) in dry pyridine (500 ml) was treated with p-toluenesulfonyl chloride (227 g) at 5°-10° C. After stirring 2 h at 10° C., the mixture was poured into ice water (2 L), followed by extraction with ethyl ether. The organic extract was washed with ice water and brine, dried, filtered and evaporated to give a syrup, which was further dried at high vacuum. The crude product was overlayered with pentane and cooled in dry ice/acetone to give a solid (210 g, 99%), mp 36°-37° C.

Workup

  1. extractionfollowed by extraction with ethyl ether
  2. extractionThe organic extract
  3. washwas washed with ice water and brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customto give a syrup, which
  8. customwas further dried at high vacuum
  9. temperaturecooled in dry ice/acetone

Sources & evidence

ORD record
ord-1b01b77d58b0472cbe68b93b4247487f
Source dataset
uspto-grants-1986_06
Patent number
US04593029

Reaction notes

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