Methanol → Methyl 5-chloro-2,3-dihydroxybenzoate

HRID 1271580Notes

Reaction equation

HRID 1271580 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:8]=[C:9]([OH:17])[C:10]([OH:16])=[C:11]([CH:15]=1)[C:12]([OH:14])=[O:13].[CH3:18]O>>[Cl:6][C:7]1[CH:8]=[C:9]([OH:17])[C:10]([OH:16])=[C:11]([CH:15]=1)[C:12]([O:14][CH3:18])=[O:13]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 123948825-Chloro-2,3-dihydroxybenzoic acid

Product 1

HCID 18613685Methyl 5-chloro-2,3-dihydroxybenzoate

Procedure

A mixture of methanol (60 ml) and sulfuric acid (5.2 ml) was stirred at room temperature. 5-Chloro-2,3-dihydroxybenzoic acid (0.11 mol) was added. The reaction mixture was stirred and refluxed for 20 hours, and then poured out onto ice. The precipitate was filtered off, washed with water, and dried, yielding 18.48 g of methyl 5-chloro-2,3-dihydroxybenzoate (intermediate 9; mp: 102° C.).

Workup

  1. stirringThe reaction mixture was stirred
  2. temperaturerefluxed for 20 hours
  3. additionpoured out onto ice
  4. filtrationThe precipitate was filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-e42f6a1ddb9e4f28a1284769ff965935
Source dataset
uspto-grants-2007_04
Patent number
US07205410B2

Reaction notes

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