4-Toluenesulfonyl chloride → HCID 20337460, compound

HRID 1706265Notes

Reaction equation

HRID 1706265 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:25]=[CH:24][C:23]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:22][C:21]=1[CH:34]([CH3:38])[CH2:35][CH2:36][OH:37])[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:37][CH2:36][CH2:35][CH:34]([C:21]1[CH:22]=[C:23]([O:26][CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:24]=[CH:25][C:20]=1[O:19][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:38])(=[O:3])=[O:2]

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 20337483HCID 20337483, compound

Product 1

HCID 20337460HCID 20337460, 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-(2,5-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 which may be purified by standard methods, if desired.

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
  5. customaffords the product which
  6. custommay be purified by standard methods

Sources & evidence

ORD record
ord-bd0a0e9356aa447eb7cced154a226d27
Source dataset
uspto-grants-1980_06
Patent number
US04206225

Reaction notes

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