2,4-Dimethoxybenzoic acid → 5-Chlorosulfonyl-2,4-dimethoxybenzoic acid

HRID 1194751Notes

Reaction equation

HRID 1194751 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].[Cl:14][S:15](O)(=[O:17])=[O:16]>>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([S:15]([Cl:14])(=[O:17])=[O:16])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]

Participants

3

Reactant 2

HCID 70522,4-Dimethoxybenzoic acidHCID 24638Chlorosulfonic acid

Product 1

HCID 167713625-Chlorosulfonyl-2,4-dimethoxybenzoic acid

Conditions

Temperature
10 °C

Procedure

1,800 ml of chlorosulphonic acid is placed in a 4 liter flask fitted with an agitator and a thermometer, and is cooled to 10° C. 328 g of finely powdered 2,4-dimethoxy benzoic acid is added in stages in the course of 45 minutes, between 10° and 15° C. The acid dissolves gradually as it is introduced. When all the acid has been added the solution is gradually heated to 55° C. and that temperature is maintained for 5 hours. The solution is left to stand overnight, then poured very slowly into 17 kg of ice, with agitation and with external cooling. The acid which is precipitated is drained, washed with water and dried in air.

Workup

  1. customfitted with an agitator
  2. dissolutionThe acid dissolves gradually as it
  3. additionis introduced
  4. additionWhen all the acid has been added the solution
  5. temperatureis gradually heated to 55° C.
  6. temperaturethat temperature is maintained for 5 hours
  7. waitThe solution is left
  8. customThe acid which is precipitated
  9. washwashed with water
  10. customdried in air

Sources & evidence

ORD record
ord-11df93e3c8a14196a36e61884364c739
Source dataset
uspto-grants-1989_03
Patent number
US04816471

Reaction notes

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