Hydrochloric Acid → 2-chloro-3,4,5-trimethoxybenzoic Acid

HRID 2230593Notes

Reaction equation

HRID 2230593 reaction equation
[Cl:1][C:2]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[C:9]([O:16][CH3:17])=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[C:9]([O:16][CH3:17])=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18464747Methyl 2-chloro-3,4,5-trimethoxybenzoate

Product 1

HCID 184647142-chloro-3,4,5-trimethoxybenzoic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine methyl 2-chloro-3,4,5-trimethoxybenzoate (2.0 g, 7.8 mmol) and a 1 M aqueous solution of sodium hydroxide (100 mL, 100 mmol) in methanol (50 mL). After 6 hours, adjust the pH to about 2 using a 1 M aqueous hydrochloric acid solution and extract with dichloromethane. Dry the combined organic layers over MgSO4, filter, and concentrate in vacuo to give the title compound: Rf=0.81 (silica gel, 10% methanol/85% c.hloroform/5% acetic acid).

Workup

  1. extractionextract with dichloromethane
  2. dry with materialDry the combined organic layers over MgSO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-0fcfe378be764b328036d2fab499c1ab
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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