Magnesium → 2-Benzofurancarboxylic acid, 6-chloro-, methyl ester

HRID 1433045Notes

Reaction equation

HRID 1433045 reaction equation
[Mg].[CH2:2]([O:4][C:5](=[O:17])[CH2:6][O:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[CH:15]=O)C>CO.Cl>[CH3:2][O:4][C:5]([C:6]1[O:7][C:8]2[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=2[CH:15]=1)=[O:17]

Participants

5

Reactant 2

HCID 5462224MagnesiumHCID 90917862HCID 90917862, compound

Product 1

HCID 713002342-Benzofurancarboxylic acid, 6-chloro-, methyl ester

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent2×

Procedure

Magnesium (1.2 g, 50 mmol) is dissolved in 40 ml of methanol. A solution of ethyl-(2-formyl-5-chloro-phenoxy)-acetate (2.1 g, 8.65 mmol) in 15 ml of methanol is added and the resulting mixture is heated under reflux for one hour, cooled, poured in 1N hydrochloric acid (150 ml). After stirring at room temperature the yellow solid is filtered, washed thoroughly with water and dried. Methyl-6-chloro-benzofurancarboxylate is obtained as a yellow solid (0.835 g, 46% yield). C10H7ClO3, MS (M+): 210, Cl pattern

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureunder reflux for one hour
  3. temperaturecooled
  4. filtrationis filtered
  5. washwashed thoroughly with water
  6. customdried

Sources & evidence

ORD record
ord-8d09236b66874d32a6049fc40be27642
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

Loading…