1,3-Butadiene → Diethyl (1R,2R)-cyclohex-4-ene-1,2-dicarboxylate

HRID 1281633Notes

Reaction equation

[CH2:1]=[CH:2][CH:3]=[CH2:4].[C:5]([O:14][CH2:15][CH3:16])(=[O:13])/[CH:6]=[CH:7]/[C:8]([O:10][CH2:11][CH3:12])=[O:9]>C1C=CC=CC=1>[C:8]([O:10][CH2:11][CH3:12])(=[O:9])[C@@H:7]1[CH2:4][CH:3]=[CH:2][CH2:1][C@H:6]1[C:5]([O:14][CH2:15][CH3:16])=[O:13]

Participants

Conditions

Temperature: 50 °C

Procedure

One hundred (100) parts by weight of a butadiene is dissolved into a solution of 153 parts of diethyl fumarate in 650 parts of benzene at 0° C. The reaction solution is then heated in a bomb at 50° C. for 24 hours. The solvent is removed by a distillation and the liquid crude product is purified by a fractional distillation under vacuum (b.p.: 102-105° C. at 2 mm);

Workup

customThe solvent is removed by a distillation
distillationthe liquid crude product is purified by a fractional distillation under vacuum (b.p.: 102-105° C. at 2 mm)

Sources & evidence

ORD record: ord-72cd6e79ae4a47eaaf9bf56168f0e400
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06454965B1

Reaction notes

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