Thionyl Chloride → o-Formylbenzenesulfonyl chloride

HRID 1040399Notes

Reaction equation

HRID 1040399 reaction equation
[Na].[S:2]([C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]=[O:9])(O)(=[O:4])=[O:3].S(Cl)([Cl:16])=O>CN(C)C=O.C(OCC)C.O>[CH:8]([C:7]1[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=1[S:2]([Cl:16])(=[O:4])=[O:3])=[O:9]

Participants

6

Reactant 2

HCID 24386Thionyl ChlorideHCID 53445294CID 53445294

Product 1

HCID 30723o-Formylbenzenesulfonyl chlorideYield 38.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-sulfobenzaldehyde sodium salt (2.0 g, 9.6 mmol) in 0.8 mL of dry N,N-dimethylformamide was added thionyl chloride (7.0 mL, 96 mmol) under nitrogen at 0° C. After being stirred at 100° C. for 3 min, the reaction mixture was diluted with diethyl ether and water at 0° C., successively. The separated organic layer was washed with water, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo to obtain crude 2-formylbenzenesulfonyl chloride (0.75 g).

Workup

  1. washThe separated organic layer was washed with water, brine
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-35c65136408f4fcb9a232a99cddef21d
Source dataset
uspto-grants-2013_10
Patent number
US08552220B2

Reaction notes

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