HCID 21427949, compound → HCID 13548054, compound

HRID 979758Notes

Reaction equation

C(C(=N[OH:14])C=C)CCCCCCCC.[CH2:15]([C:24](=[CH2:27])[C:25]#[N:26])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>CC1C=CC=CC=1C>[CH2:15]([C:24](=[CH2:27])[C:25]([NH2:26])=[O:14])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

Conditions

Temperature: -20 °C

Procedure

418.8 g of 94% pure α-nonylacrolein oxime, 1,030 g of o-xylene, 94.6 g of 95% pure α-nonylacrylonitrile and 13.9 g (2 mol %, based on oxime) of Cu(II) 2-ethylhexanoate were heated at 130° C. A vigorous exothermic reaction began; after this reaction had abated, stirring was continued for a further 1.5 hours at 110° C. Analysis by gas chromatography showed that 98.8% of the oxime used had been converted. 1.2 liters of petroleum ether were added to the reaction mixture, the latter was then cooled to -20° C., and the crude amide precipitated was filtered off under suction. Recrystallization from cyclohexane gave 332 g (84%) of α-nonylacrylamide as colorless crystals of melting point 80°-81° C.

Workup

customA vigorous exothermic reaction
customthe crude amide precipitated
filtrationwas filtered off under suction
customRecrystallization from cyclohexane

Sources & evidence

ORD record: ord-0668ec319f7e4cf4b66f65f84d759699
Source dataset: uspto-grants-1987_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04634558

Reaction notes

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