N,N,N',N'-Tetramethylmethanediamine → 5-((Dimethylamino)methyl)-2-furanmethanol

HRID 67879

Reaction equation

HRID 67879 reaction equation
[CH3:1][N:2]([CH2:4]N(C)C)[CH3:3].[O:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH2:13][OH:14]>C(O)(=O)C>[CH3:1][N:2]([CH2:4][C:12]1[O:8][C:9]([CH2:13][OH:14])=[CH:10][CH:11]=1)[CH3:3]

Participants

4

Reactant 2

HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 7361Furfuryl Alcohol

Product 1

HCID 849065-((Dimethylamino)methyl)-2-furanmethanolYield 94%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bis(dimethylamino)methane (112 g, 1.1 mol) in acetic acid (200 ml) was added dropwise with cooling (10° C.) to a stirred solution of 2-furanmethanol (98 g, 1.0 mol) in acetic acid (1000 ml). The mixture was stirred at room temperature for 18 hours and acetic acid was removed at 60° C. under reduced pressure. Ice (200 g) was added to the residue which was made basic with 40% aqueous sodium hydroxide (with external cooling). The mixture was extracted with ethyl acetate and the extracts were evaporated and distilled to give 5-dimethylaminomethyl-2-furanmethanol (145 g, 94%) b.p. 92°-96° C./0.2 0.5 mmHg.

Workup

  1. customacetic acid was removed at 60° C. under reduced pressure
  2. additionIce (200 g) was added to the residue which
  3. extractionThe mixture was extracted with ethyl acetate
  4. customthe extracts were evaporated
  5. distillationdistilled

Sources & evidence

ORD record
ord-06afed7af5584767adb5809322c8679e
Source dataset
uspto-grants-1982_08
Patent number
US04347191

Linked notes

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