Sodium Chloride → 5-Chlorosulphonyl-2-anisic acid

HRID 1589354Notes

Reaction equation

HRID 1589354 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].ClC(Cl)C.[C:10]([OH:20])(=[O:19])[C:11]1[C:12]([O:17][CH3:18])=[CH:13][CH:14]=[CH:15][CH:16]=1.[Cl-].[Na+]>>[Cl:1][S:2]([C:15]1[CH:14]=[CH:13][C:12]([O:17][CH3:18])=[C:11]([CH:16]=1)[C:10]([OH:20])=[O:19])(=[O:5])=[O:3]

Participants

5

Reactant 4

HCID 5234Sodium ChlorideHCID 63651,1-DichloroethaneHCID 113702-Methoxybenzoic acidHCID 24638Chlorosulfonic acid

Product 1

HCID 1040075-Chlorosulphonyl-2-anisic acidYield 65%

Procedure

Chlorosulphonic acid (55 ml) was added over 6 hrs at 20° to a stirred mixture of dichloroethane (72 ml), o-anisic acid (26.8 g) and sodium chloride (10 g). The mixture was warmed to 40° and after a further hour warmed to 65°. The mixture was maintained at 65°-70° for 17 hrs, cooled and poured into ice water (300 g) to give the title compound as a colourless solid (28.7 g; 65%). ##STR16##

Workup

  1. temperatureThe mixture was warmed to 40° and after a further hour
  2. temperaturewarmed to 65°
  3. temperatureThe mixture was maintained at 65°-70° for 17 hrs
  4. temperaturecooled

Sources & evidence

ORD record
ord-595cc819c28c45f094ac4aa4da6ecb1e
Source dataset
uspto-grants-1986_02
Patent number
US04569940

Reaction notes

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