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

HRID 1421818Notes

Reaction equation

HRID 1421818 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 (3.68 g, 26.29 mmol) in methanol (30 ml) was treated with a solution of potassium hydroxide (2.80 g, 50.0 mmol) in water (15 ml) and the mixture stirred for 2 h 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 (×3). The combined organic solutions were dried and concentrated to yield the title compound as a yellow solid (3.12 g, 94%); m.p. 110-112° C.; (Found: M+, 126.0312. C6H6O3 requires M+ 126.0317); νmax (CH2Cl2) 3300-2700, 1688, 1524, 1424, 1305, 1210 and 1167 cm-1 ; δH (CDCl3, 90 MHz) 2.40 (3H, s), 6.15 (1H, d, J 4 Hz) and 7.22 (1H, d, J 4 Hz).

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 (×3)
  5. customThe combined organic solutions were dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-367aa7ab638c4284be45d28f8bf24fcb
Source dataset
uspto-grants-2000_06
Patent number
US06077952

Reaction notes

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