Water → 51521-75-6

HRID 1606598Notes

Reaction equation

HRID 1606598 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[S:12]([OH:14])=[O:13].O.[OH-].[Na+].[CH3:18]I>CO>[Cl:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([S:12]([CH3:18])(=[O:14])=[O:13])=[CH:4][C:5]=1[C:9]([OH:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14798Sodium Hydroxide2×HCID 215439462,4-Dichloro-5-carboxybenzenesulfinic acid

Product 1

HCID 2210136551521-75-6Yield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product of Step A is placed in a three-liter flask to which is added water (300 ml.), methanol (500 ml.) sufficient 10N sodium hydroxide to attain a pH of 9 and methyl iodide (520 g.; 3.66 moles). The reaction mixture is refluxed for 36 hours with the occasional addition of 10N sodium hydroxide to maintain pH 9. The alcohol is distilled at reduced pressure and the reaction solution is acidified with hydrochloric acid. The product is filtered, washed with water, dried and recrystallized from ethanol (800 ml.) to give 150 g. (yield 56%) 2,4-dichloro-5-methylsulfonylbenzoic acid, m.p. 210°-211° C.

Workup

  1. temperatureto maintain pH 9
  2. distillationThe alcohol is distilled at reduced pressure
  3. filtrationThe product is filtered
  4. washwashed with water
  5. customdried
  6. customrecrystallized from ethanol (800 ml.)
  7. customto give 150 g

Sources & evidence

ORD record
ord-d2dc177b488d44038a5f7b0a323ec066
Source dataset
uspto-grants-1976_04
Patent number
US03953476

Reaction notes

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