Potassium Hydroxide → 2-Furancarboxylic acid, 5-methyl-

HRID 376597

Reaction equation

HRID 376597 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]([O:9]C)=[O:8])=[CH:4][CH:3]=1.[OH-].[K+]>CO.O>[CH3:1][C:2]1[O:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 137628Methyl 5-methyl-2-furancarboxylate

Product 1

HCID 747102-Furancarboxylic acid, 5-methyl-Yield 94.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 5-methyl-2-furoate (3.68g, 26.29mmol) in methanol (30ml) was treated with a solution of potassium hydroxide (2.80g, 50.0mmol) in water (15ml) and the mixture stirred for 2h at room temperature. The methanol was evaporated in vacuo, the residue dissolved in water and washed with ethyl acetate. The aqueous phase was acidified with 5N hydrochloric acid, and the product extracted with ethyl acetate (x3). The combined organic solutions were dried and concentrated to yield the title compound as a yellow solid (3.12g, 94%); m.p. 110-112° C.; (Found: M+, 126.0312. C6H6O3 requires M+ 126.0317); vmax (CH2Cl2) 3300-2700, 1688, 1524, 1424, 1305, 1210 and 1167cm-1 ; δH (CDCl3 , 90MHz) 2.40 (3H, s), 6.15 (1H, d, J 4Hz) and 7.22 (1H, d, J 4Hz).

Workup

  1. customThe methanol was evaporated in vacuo
  2. dissolutionthe residue dissolved in water
  3. washwashed with ethyl acetate
  4. extractionthe product extracted with ethyl acetate (x3)
  5. customThe combined organic solutions were dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-07ff8995c81942eca8a9d0f8719f92ed
Source dataset
uspto-grants-2000_02
Patent number
US06020329

Linked notes

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