Isobutanol → ((1E)-4,4-dimethoxy-3-oxobut-1-en-1-yl)dimethylamine

HRID 1897307Notes

Reaction equation

HRID 1897307 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[CH3:9][O:10][C:11]([O:15][CH3:16])(C)[CH:12]=[O:13].[CH2:17](O)C(C)C>>[CH3:5][N:4]([CH3:6])/[CH:3]=[CH:17]/[C:12](=[O:13])[CH:11]([O:15][CH3:16])[O:10][CH3:9]

Participants

4

Reactant 3

HCID 6560IsobutanolHCID 78373Dimethylformamide dimethyl acetalHCID 75681812,2-Dimethoxypropanal

Product 1

HCID 5709580((1E)-4,4-dimethoxy-3-oxobut-1-en-1-yl)dimethylamineYield 48%

Conditions

Temperature
100 °C

Procedure

A mixture of N,N-dimethylformamide dimethylacetal (86.0 g, 584 mmol) and methylglyoxal 1,1-dimethylacetal (85.6 g, 724 mmol) in isobutanol (500 mL) was heated at 100° C. overnight. The mixture was then cooled and evaporated. Purification by distillation afforded the title product (49.9 g, 48%) as an orange liquid. Bp 123-124° C. at 0.9 mbar. MS: m/e=174.4 [M+H]+.

Workup

  1. temperatureThe mixture was then cooled
  2. customevaporated
  3. customPurification
  4. distillationby distillation

Sources & evidence

ORD record
ord-437bdd284ee1456991bc3c23fe3d708a
Source dataset
uspto-grants-2013_08
Patent number
US08518974B2

Reaction notes

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