2-Methoxybenzoic acid → 5-Chlorosulphonyl-2-anisic acid

HRID 2182844Notes

Reaction equation

HRID 2182844 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].[S:12]([Cl:16])(=O)(=[O:14])[OH:13]>>[Cl:16][S:12]([C:9]1[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[C:4]([CH:8]=1)[C:5]([OH:7])=[O:6])(=[O:14])=[O:13]

Participants

3

Reactant 2

HCID 113702-Methoxybenzoic acidHCID 24638Chlorosulfonic acid

Product 1

HCID 1040075-Chlorosulphonyl-2-anisic acidYield 58.2%

Procedure

2-Methoxybenzoic acid (available from Aldrich, 5.0 g, 32.9 mmol) was warmed with chlorosulfuric acid (164 mmol, 5.0 eq., 19.1 g, 11.0 mmol) at 50° C. for 2 h. The resulting thick brown liquid was poured on crushed ice with vigorous stirring. The resulting white precipitates were filtered, washed with H2O, and dried overnight under high vacuum to give Intermediate 6 (4.8 g, 58%) as a white powder.

Workup

  1. additionThe resulting thick brown liquid was poured
  2. customon crushed ice with vigorous stirring
  3. customThe resulting white precipitates
  4. filtrationwere filtered
  5. washwashed with H2O
  6. customdried overnight under high vacuum

Sources & evidence

ORD record
ord-926a0fe5ad0547519490b0e8acec55d7
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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