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

Participants

Role	Name	HCID	Charge
Reactant	Isobutanol	HCID 6560	—
Reactant	Dimethylformamide dimethyl acetal	HCID 78373	—
Reactant	2,2-Dimethoxypropanal	HCID 7568181	—
Product	((1E)-4,4-dimethoxy-3-oxobut-1-en-1-yl)dimethylamine	HCID 5709580	48%

Reaction Conditions

Temperature	100 °C

Reaction Steps

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]|.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08846719B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-3adff59fadee4f15adb97eab48785b0d
Source note	uspto-grants-2014_09