Ethyl 2,4-dimethyl-3-furoate → (2,4-Dimethylfuran-3-yl)methanol

HRID 1855794Notes

Reaction equation

HRID 1855794 reaction equation
[CH3:1][C:2]1[O:3][CH:4]=[C:5]([CH3:12])[C:6]=1[C:7](OCC)=[O:8].[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH3:1][C:2]1[O:3][CH:4]=[C:5]([CH3:12])[C:6]=1[CH2:7][OH:8]

Participants

4

Reactant 2

HCID 579770Ethyl 2,4-dimethyl-3-furoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 12858598(2,4-Dimethylfuran-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

2,4-Dimethyl-3-carbethoxyfuran (42.8 g.) prepared in accordance with J. Amer. Chem. Soc., v. 73, 356 (1951) was dissolved in ether (100 ml.) and added slowly to a cooled (0°) slurry of lithium aluminum hydride (10 g.) in ether (200 ml.) and the mixture was then stirred at room temperature for 18 hours. After this time, the mixture was cooled in an ice bath and quenched with an aqueous solution of sodium sulfate (60 ml.; saturated) followed by the addition of solid magnesium sulfate. The solids were filtered off, washed well with additional ether and the combined ether extract was concentrated to yield 2,4-dimethyl-3-hydroxymethylfuran. Distillation gave pure 2,4-dimethyl-3-hydroxymethylfuran (21.1 g.) bp 63°-65° at 2 mm Hg.

Workup

  1. additionadded slowly to
  2. temperatureAfter this time, the mixture was cooled in an ice bath
  3. customquenched with an aqueous solution of sodium sulfate (60 ml.; saturated)
  4. additionfollowed by the addition of solid magnesium sulfate
  5. filtrationThe solids were filtered off
  6. washwashed well with additional ether
  7. extractionthe combined ether extract
  8. concentrationwas concentrated

Sources & evidence

ORD record
ord-33e0f1944d044a8ba32cee0c4f0f8306
Source dataset
uspto-grants-1980_08
Patent number
US04216312

Reaction notes

Loading…