Benzenesulfonyl chloride → HCID 86739849, compound

HRID 1154558Notes

Reaction equation

HRID 1154558 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:5]([CH:6]=[O:7])[C:4]=1[OH:11].[C:12]1([S:18](Cl)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>[OH-].[Na+]>[OH:11][C:4]1[C:3]([O:2][CH3:1])=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7].[CH:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[S:18]([O-:20])(=[O:2])=[O:19]

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 8991o-Vanillin

Product 1

HCID 86739849HCID 86739849, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A slurry of 3-methoxysalicylaldehyde (45.6 g, 299 mM) in NaOH (138 ml, 15% aqueous solution) is treated with benzenesulfonyl chloride (66 g, 373 mM) and the mixture vigorously stirred for 1 hour. The reaction mixture is then poured into ice-water (500 ml) and the resulting white solid filtered, washed with cold water, and then recrystallized from acetic acid to afford the product as a white solid; yield 72.2 g (85%); m.p. 119°-120° C.

Workup

  1. filtrationthe resulting white solid filtered
  2. washwashed with cold water
  3. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-706b7573d7cb4621b11dfe4757f8d030
Source dataset
uspto-grants-1984_12
Patent number
US04490374

Reaction notes

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