Methyl Salicylate → Methyl 5-(chlorosulfonyl)-2-hydroxybenzoate

HRID 1623682Notes

Reaction equation

HRID 1623682 reaction equation
[S:1]([Cl:5])(=O)(=[O:3])[OH:2].[OH:6][C:7]1[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10]>>[Cl:5][S:1]([C:14]1[CH:15]=[CH:16][C:7]([OH:6])=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10])(=[O:3])=[O:2]

Participants

3

Reactant 2

HCID 4133Methyl SalicylateHCID 24638Chlorosulfonic acid

Product 1

HCID 12581955Methyl 5-(chlorosulfonyl)-2-hydroxybenzoate

Conditions

Temperature
0 °C

Procedure

Sulfurochloridic acid (38.3 g, 329 mmol) at 0° C. was added to methyl 2-hydroxybenzoate (10 g, 65.7 mmol) in small portions and the mixture was then stirred at 0° C. for 1 h. The mixture was added dropwise to 10 ml ice-water with stirring and stirring continued for an additional 0.5 h. The ensuing white crystals were collected by filtration, washed three times with water, and then dried to yield the title compound. 12 g.

Workup

  1. stirringwith stirring
  2. stirringstirring
  3. waitcontinued for an additional 0.5 h
  4. filtrationThe ensuing white crystals were collected by filtration
  5. washwashed three times with water
  6. customdried

Sources & evidence

ORD record
ord-d71d3aba790743c98162c3f549b8f3bd
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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