Oxalyl chloride → 4-(Benzyloxy)benzene-1-sulfonyl chloride

HRID 1620378Notes

Reaction equation

HRID 1620378 reaction equation
C(Cl)(=O)C([Cl:4])=O.[Na].[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([OH:25])(=O)=[O:23])=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>ClCCl.CN(C)C=O>[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([Cl:4])(=[O:25])=[O:23])=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 5360545SodiumHCID 113351434-(Benzyloxy)benzenesulfonic acid

Product 1

HCID 47383854-(Benzyloxy)benzene-1-sulfonyl chlorideYield 89%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 55 ml (639 mmol) of oxalyl chloride in 250 ml of dichloromethane is added dropwise to a solution of 61 g (213 mmol) of the sodium salt of 4-benzyloxybenzenesulfonic acid in 200 ml of dimethylformamide, while maintaining the temperature between −20° C. and −10° C. After addition, the reaction medium is slowly brought back to ambient temperature and then stirred for 18 h, poured onto ice and extracted with ethyl acetate. The organic phase is washed with water and with a saturated aqueous solution of sodium chloride and concentrated under vacuum. 54 g (89%) of 4-benzyloxybenzenesulfonyl chloride are obtained in the form of a white solid.

Workup

  1. temperaturewhile maintaining the temperature between −20° C. and −10° C
  2. additionAfter addition
  3. customis slowly brought back to ambient temperature
  4. additionpoured onto ice
  5. extractionextracted with ethyl acetate
  6. washThe organic phase is washed with water and with a saturated aqueous solution of sodium chloride
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7349e290272740bda0036fb08fe292e7
Source dataset
uspto-grants-2014_07
Patent number
US08772478B2

Reaction notes

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