4-Toluenesulfonyl chloride → HCID 20487396, compound

HRID 435132Notes

Reaction equation

HRID 435132 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:34]([CH3:38])[CH2:35][CH2:36][OH:37])[CH:23]=[C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:25]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>N1C=CC=CC=1.Cl>[CH2:27]([O:26][C:24]1[CH:23]=[C:22]([CH:34]([CH3:38])[CH2:35][CH2:36][O:37][S:1]([C:4]2[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=2)(=[O:3])=[O:2])[CH:21]=[C:20]([O:19][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:25]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 13243718HCID 13243718, compound

Product 1

HCID 20487396HCID 20487396, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Procedure

Tosyl chloride (11.1 g., 58.1 mM) is added to a solution of 3-(3,5-dibenzyloxyphenyl)-1-butanol (20.7 g., 57 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. Yield: 24.63 g. (84%).

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-b38249b024ca40c18d3dfb051b29d443
Source dataset
uspto-grants-1983_08
Patent number
US04400385

Reaction notes

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