Hydrochloric Acid → 6-Methoxy-1-benzofuran-2-carboxylic acid

HRID 1904884Notes

Reaction equation

HRID 1904884 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.Br[CH:13](C([O-])=O)[C:14]([O:16]CC)=[O:15].C(=O)([O-])[O-].[K+].[K+].[OH-].[K+].Cl>CO.CC(CC)=O>[CH3:11][O:10][C:8]1[CH:7]=[CH:6][C:3]2[CH:4]=[C:13]([C:14]([OH:16])=[O:15])[O:1][C:2]=2[CH:9]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 696002-Hydroxy-4-MethoxybenzaldehydeHCID 57352664HCID 57352664, compound

Product 1

HCID 9188636-Methoxy-1-benzofuran-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

11 g of 2-hydroxy-4-methoxybenzaldehyde, 20.3 g of ethyl bromomalonate, 12.3 g of potassium carbonate, and 51 ml of methyl-ethyl ketone were put into a three-necked flask, and refluxed to hold the reaction thereof for 6 hours. After that to this was added a methanol solution of potassium hydroxide, and at a point of time of completion of the hydrolysis reaction, the hydrolyzed product was put into an aqueous hydro chloric acid solution, and then filtered, whereby a 6-methoxy-benzofuran-2-carboxylic acid having a melting point between 208° C. and 211° C. was obtained.

Workup

  1. temperaturerefluxed
  2. customthe reaction
  3. customat a point of time of completion of the hydrolysis reaction
  4. filtrationfiltered

Sources & evidence

ORD record
ord-618d4f2a93d4417fb53a523313dc160d
Source dataset
uspto-grants-1989_06
Patent number
US04840869

Reaction notes

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