Formaldehyde → HCID 21523290, compound

HRID 918159Notes

Reaction equation

HRID 918159 reaction equation
[CH2:1]([OH:5])[CH:2]([CH3:4])[CH3:3].[CH2:6]([NH:13][CH3:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C=O.[C:17](=O)([O-])[O-].[K+].[K+]>>[CH2:1]([O:5][CH2:14][N:13]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:17])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 6560IsobutanolHCID 7669N-MethylbenzylamineHCID 11430Potassium Carbonate

Product 1

HCID 21523290HCID 21523290, compound

Procedure

To a solution of isobutanol (19.2 g., 0.26 mole) and N-benzyl-N-methylamine (30 g., 0.25 mole) is added excess 40 percent formaldehyde (25 g.). The mixture reacts exothermically, and two layers form. Potassium carbonate is added to form a saturated aqueous layer. The mixture is stirred overnight, then extracted thoroughly with diethyl ether. The ether layer is dried, then evaporated under vacuum to provide a residual oil. The residue is distilled under vacuum to provide N-benzyl-N-methylaminomethyl isobutyl ether, b.p. 72°-77° C. at 1.5 mm. Hg as a clear liquid. The structure is established by nuclear magnetic resonance analysis.

Workup

  1. customThe mixture reacts exothermically
  2. customtwo layers form
  3. customto form a saturated aqueous layer
  4. extractionextracted thoroughly with diethyl ether
  5. dry with materialThe ether layer is dried
  6. customevaporated under vacuum
  7. customto provide a residual oil
  8. distillationThe residue is distilled under vacuum

Sources & evidence

ORD record
ord-da7799cdd0ad4f38a1843921dc591140
Source dataset
uspto-grants-1976_07
Patent number
US03969467

Reaction notes

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