5-Methylfurfural → 2-Furancarboxylic acid, 5-methyl-

HRID 1355904Notes

Reaction equation

HRID 1355904 reaction equation
[OH-:1].[Na+].BrBr.[CH3:5][C:6]1[O:10][C:9]([CH:11]=[O:12])=[CH:8][CH:7]=1>O>[CH3:5][C:6]1[O:10][C:9]([C:11]([OH:1])=[O:12])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 120975-MethylfurfuralHCID 14798Sodium HydroxideHCID 24408Bromine

Product 1

HCID 747102-Furancarboxylic acid, 5-methyl-Yield 60.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Following the method of Shapiro et al. (Khim. Geterotsikl. Soedin. 1982, 11, 1463), to a stirred solution of 80.3 g (2.00 mol) sodium hydroxide in 330 ml water at 0-5° C. was added dropwise 18 ml (0.35 mol) bromine. 25 ml (0.25 mol) 5-methyl-2-furfural was then added dropwise over 90 minutes and stirring continued for a further 45 minutes at 0-5° C. The reaction mixture was then extracted with ether and the phases separated. The aqueous phase was acidified to pH 1 with concentrated hydrochloric acid and the resulting precipitate collected by filtration and dried in vacuo to afford 19.1 g (60%) 5-methyl-2-furoic acid as a beige crystalline solid. 1H NMR δ (CDCl3, 250 MHz): 8.00-6.60 (1H, v. br. s), 7.24 (1H, d, J=3.4 Hz), 6.17 (1H, d, J=3.4 Hz), 2,42 (3H, s).

Workup

  1. extractionThe reaction mixture was then extracted with ether
  2. customthe phases separated
  3. filtrationthe resulting precipitate collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-709990bdbaf34e819172768ec7079006
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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