Formaldehyde → 5-[2-(N,N-Dimethylamino)ethyl]-2-furanmethanol

HRID 65737Notes

Reaction equation

HRID 65737 reaction equation
[CH3:1][N:2]([CH3:10])[CH2:3][CH2:4][C:5]1[O:6][CH:7]=[CH:8][CH:9]=1.[CH2:11]=[O:12].[OH-].[Na+]>C(O)(=O)C>[CH3:1][N:2]([CH2:3][CH2:4][C:5]1[O:6][C:7]([CH2:11][OH:12])=[CH:8][CH:9]=1)[CH3:10]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 38131N,N-Dimethyl-2-furanethanamine

Product 1

HCID 234521095-[2-(N,N-Dimethylamino)ethyl]-2-furanmethanol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N,N-Dimethyl-2-furanethanamine (9.8 g), 30% aqueous formaldehyde (17.5 g) and glacial acetic acid (18 ml) were heated at 70° for 5 hr. The reaction was cooled, basified with sodium hydroxide and extracted with ether. The organic extracts were distilled to give an oil b.p. 90°-100° (0.5 mm). Found: C, 64.0; H, 8.9; N, 8.0. C9H15NO2 requires: C, 63.9; H, 8.9; N, 8.2%.

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with ether
  3. distillationThe organic extracts were distilled

Sources & evidence

ORD record
ord-ac50d86fe34f4d0ab69b47e9b611bca3
Source dataset
uspto-grants-1978_12
Patent number
US04128658

Reaction notes

Loading…