Furfuryl Alcohol → 5-[(Methylamino)methyl]-2-furanmethanol

HRID 65736

Reaction equation

HRID 65736 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6]O.Cl.[CH3:9][NH2:10].[C:11](=[O:14])([O-])[O-].[Na+].[Na+]>C=O>[CH3:9][NH:10][CH2:6][C:2]1[O:1][C:5]([CH2:11][OH:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7361Furfuryl AlcoholHCID 10340Sodium CarbonateHCID 6364545Methylamine hydrochloride

Product 1

HCID 146717475-[(Methylamino)methyl]-2-furanmethanol

Reagents, catalysts & solvents 1

HCID 712FormaldehydeSolvent

Procedure

A mixture of 2-furanmethanol (49 g), methylamine hydrochloride (51.5 g) and 36% formaldehyde solution (50 ml) was stirred at 0°-3° for 3 hr and allowed to stand for 16 hr. Excess sodium carbonate was added and the slurry extracted with ethyl acetate. After removal of solvent the residue was distilled to give 5-(methylamino)methyl-2-furanmethanol (36.2 g) b.p. 111°-113° (0.2 mm).

Workup

  1. waitto stand for 16 hr
  2. extractionthe slurry extracted with ethyl acetate
  3. customAfter removal of solvent the residue
  4. distillationwas distilled

Sources & evidence

ORD record
ord-d367991a172444eabb875f75fdc2f518
Source dataset
uspto-grants-1978_12
Patent number
US04128658

Linked notes

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