HCID 67401930, compound → 183324-68-7

HRID 906090Notes

Reaction equation

HRID 906090 reaction equation
[CH3:1][C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[CH:4][C:3]=1[C:11]([O:13]C)=[O:12]>[OH-].[K+].CO>[CH3:1][C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[CH:4][C:3]=1[C:11]([OH:13])=[O:12]

Participants

3

Reactant 1

HCID 67401930HCID 67401930, compound

Product 1

HCID 57748447183324-68-7Yield 75.1%

Reagents, catalysts & solvents 1

HCID 23689386Potassium hydroxide methanolSolvent

Procedure

A solution of methyl 7-methyl-1-benzofuran-6-carboxylate (370 mg, 1.95 mmol) in 35% aqueous potassium hydroxide/methanol (1:3, 4 mL) was stirred at reflux for 30 minutes. The methanol was removed under reduced pressure and resultant aqueous portion was brought to pH 2 using 6N aqueous hydrochloric acid. The precipitate which formed was collected by filtration and dried in vacuo to afford (258 mg, 75%) of 7-methyl-1-benzofuran-6-carboxylic acid. 1H NMR (400 MHz, DMSO-d6): 8.17 (d, 1H), 7.78 (d, 1H), 7.54 (d, 1H), 7.03 (d, 1H), 2.72 (s, 3H). MS (EI) for C10H8O3: 177 (MH+).

Workup

  1. temperatureat reflux for 30 minutes
  2. customThe methanol was removed under reduced pressure
  3. customThe precipitate which formed
  4. filtrationwas collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-602834f9817342d3ba9d26c21c6bcb50
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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