Methanol → 2-Chloro-3-(hydroxymethyl)-4-methylsulfonylbenzoic acid

HRID 1682155Notes

Reaction equation

HRID 1682155 reaction equation
[OH-].[Na+].C([O:6][CH2:7][C:8]1[C:9]([Cl:22])=[C:10]([CH:15]=[CH:16][C:17]=1[S:18]([CH3:21])(=[O:20])=[O:19])[C:11]([O:13]C)=[O:12])(=O)C.CO>O>[Cl:22][C:9]1[C:8]([CH2:7][OH:6])=[C:17]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:16]=[CH:15][C:10]=1[C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 19804727HCID 19804727, compound

Product 1

HCID 151328832-Chloro-3-(hydroxymethyl)-4-methylsulfonylbenzoic acidYield 40.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6 ml of an aqueous solution containing 1.3 g of sodium hydroxide (93%), was added to 3.9 g of methyl 3-acetoxymethyl-2-chloro-4-methanesulfonylbenzoate and 100 ml of methanol. The mixture was stirred for 30 minutes at room temperature. 50 ml of water was added thereto, and methanol was distilled off under reduced pressure. Then, the reaction mixture was acidified with hydrochloric acid and extracted with chloroform. The extract was concentrated to dryness to obtain 1.3 g of the desired product. Melting point: 240°-245° C.

Workup

  1. distillationmethanol was distilled off under reduced pressure
  2. extractionextracted with chloroform
  3. concentrationThe extract was concentrated to dryness

Sources & evidence

ORD record
ord-3481b55b74f645aa9c4641e49e955cfd
Source dataset
uspto-grants-1992_12
Patent number
US05175299

Reaction notes

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