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

HRID 1264650Notes

Reaction equation

HRID 1264650 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-70915e134a844ed1b78dfc4e36e9fbde
Source dataset
uspto-grants-2003_04
Patent number
US06544997B1

Reaction notes

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