Hydrochloric Acid → 5-Methylfuran-3-carboxylic acid

HRID 1952856Notes

Reaction equation

HRID 1952856 reaction equation
[CH3:1][C:2]1[O:6][CH:5]=[C:4]([C:7]([O:9]CC)=[O:8])[CH:3]=1.[OH-].[K+].Cl>O>[CH3:1][C:2]1[O:6][CH:5]=[C:4]([C:7]([OH:9])=[O:8])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 12332585Ethyl 5-methylfuran-3-carboxylate

Product 1

HCID 1793795-Methylfuran-3-carboxylic acidYield 91.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

A mixture of 31.7 g (206 mmol) of ethyl 5-methylfuran-3-carboxylate, 40 ml of 45% strength potassium hydroxide and 100 ml of water was refluxed for 4 h, then cooled to 10° C. and acidified to pH 1 with 15% strength hydrochloric acid. The resulting mixture was left at this temperature for 2 h, and the precipitate was filtered off and dried to constant weight at 45-50° C., resulting in 23.7 g (188 mmol, 91%) of 5-methylfuran-3-carboxylic acid.

Workup

  1. temperaturewas refluxed for 4 h
  2. filtrationthe precipitate was filtered off
  3. customdried to constant weight at 45-50° C.

Sources & evidence

ORD record
ord-7840415ec1db4da8883176945e9f6a36
Source dataset
uspto-grants-2000_09
Patent number
US06114358

Reaction notes

Loading…