4-Toluenesulfonyl chloride → HCID 20496824, compound

HRID 225189Notes

Reaction equation

HRID 225189 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[CH2:12]([O:19][C:20]1[CH:21]=[C:22]([CH:26]([CH3:30])[CH2:27][CH2:28][OH:29])[CH:23]=[CH:24][CH:25]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>N1C=CC=CC=1.Cl>[S:1]([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)([O:29][CH2:28][CH2:27][CH:26]([C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([O:19][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:21]=1)[CH3:30])(=[O:3])=[O:2]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 147426233-(3-Benzyloxyphenyl)-1-butanol

Product 1

HCID 20496824HCID 20496824, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Procedure

Tosyl chloride (9.8 g., 51 mM) is added to a solution of 3-(3-benzyloxyphenyl)-1-butanol (12.8 g., 50 mM) in pyridine (90 ml.) at -45° C. The reaction mixture is held at -35° C. for 18 hours and is then diluted with cold 2 N hydrochloric acid (1500 ml.) and extracted with ether (5×250 ml.). The combined extracts are washed with saturated sodium chloride solution (4×250 ml.) and then dried (Na2SO4). Concentration of the dried extract affords the product as an oil. It is crystallized by treatment with ether-hexane.

Workup

  1. extractionextracted with ether (5×250 ml.)
  2. washThe combined extracts are washed with saturated sodium chloride solution (4×250 ml.)
  3. dry with materialdried (Na2SO4)
  4. extractionConcentration of the dried extract

Sources & evidence

ORD record
ord-7fb7549cedc74805aac3a45ba883188b
Source dataset
uspto-grants-1980_11
Patent number
US04235913

Reaction notes

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