2-Methylbenzoic acid → 5-(Chlorosulfonyl)-2-methylbenzoic acid

HRID 855999

Reaction equation

HRID 855999 reaction equation
[C:1]1([CH3:10])[C:2]([C:7]([OH:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[Cl:11][S:12](O)(=[O:14])=[O:13]>>[Cl:11][S:12]([C:4]1[CH:5]=[CH:6][C:1]([CH3:10])=[C:2]([CH:3]=1)[C:7]([OH:9])=[O:8])(=[O:14])=[O:13]

Participants

3

Reactant 2

HCID 83732-Methylbenzoic acidHCID 24638Chlorosulfonic acid

Product 1

HCID 3084495-(Chlorosulfonyl)-2-methylbenzoic acidYield 78%

Conditions

Temperature
100 °C

Procedure

A mixture of o-toluic acid (15 g, 0.11 mol) and chlorosulfonic acid (30 ml) was heated at 100° C. under nitrogen for 2.5 h. The reaction mixture was then poured onto ice (500 ml) and the resulting precipitate was filtered, yielding the title compound as an off-white solid (20 g, 78% yield). MP 151–155° C.

Workup

  1. additionThe reaction mixture was then poured onto ice (500 ml)
  2. filtrationthe resulting precipitate was filtered

Sources & evidence

ORD record
ord-d3765ec8103243a7987162440440850c
Source dataset
uspto-grants-2007_08
Patent number
US07262318B2

Linked notes

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