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

HRID 1533442Notes

Reaction equation

HRID 1533442 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].[Cl:12][S:13](O)(=[O:15])=[O:14].S(Cl)(Cl)=O>>[Cl:12][S:13]([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:15])=[O:14]

Participants

4

Reactant 3

HCID 113702-Methoxybenzoic acidHCID 24386Thionyl ChlorideHCID 24638Chlorosulfonic acid

Product 1

HCID 1040075-Chlorosulphonyl-2-anisic acidYield 94%

Procedure

Commercially available 2-methoxybenzoic acid (15.2 g, 0.1 mol) was added portionwise to chlorosulphonic acid (52.43 g) over 30 min with ice cooling. Thionyl chloride (11.9 g, 0.1 mol) was added and the reaction stirred overnight. The reaction was quenched onto ice/water (250 g/65 ml) and the precipitated product granulated for 1 hr, filtered, water washed and oven dried to give the title compound (23.56 g, 93.9%) as a white solid with m.p. 138-140° C. δ (CDCl3): 4.18 (3H, s), 7.23 (1H, d), 8.21 (1H, d), 8.78 (1H, s).

Workup

  1. customThe reaction was quenched onto ice/water (250 g/65 ml)
  2. waitthe precipitated product granulated for 1 hr
  3. filtrationfiltered
  4. washwater washed
  5. customoven dried

Sources & evidence

ORD record
ord-1f33fea2fdca412caad03687db456617
Source dataset
uspto-grants-2001_03
Patent number
US06207829B1

Reaction notes

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