Methanol → 2-Chloro-5-iodo-4-methyl-benzoic acid methyl ester

HRID 522147Notes

Reaction equation

HRID 522147 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([I:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:18]O>>[Cl:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([I:12])=[CH:7][C:3]=1[C:4]([O:6][CH3:18])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 1068618952-Chloro-5-iodo-4-methylbenzoic acid

Product 1

HCID 1068618982-Chloro-5-iodo-4-methyl-benzoic acid methyl esterYield 88%

Conditions

Temperature
60 °C

Procedure

To a solution of 2-chloro-5-iodo-4-methylbenzoic acid (Preparation 49, 2.50 g, 8.43 mmol) in methanol (50 mL) was added concentrated sulfuric acid (1.2 mL) and the reaction was heated at 60° C. for 18 hours. The reaction was cooled, concentrated in vacuo, diluted with water and basified with potassium carbonate until pH=9. The aqueous solution was extracted with EtOAc (3×100 mL), the organic layers combined, washed with water (100 mL), brine (100 mL), dried over magnesium sulphate and concentrated in vacuo to afford the title compound (2.3 g, 88%).

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated in vacuo
  3. additiondiluted with water
  4. extractionThe aqueous solution was extracted with EtOAc (3×100 mL)
  5. washwashed with water (100 mL), brine (100 mL)
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-846f0a723dc646c5b5d61261274e5bdb
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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