Propanedioic acid, dibutyl ester → Di-n-butyl 2-vinylcyclopropane-1,1-dicarboxylate

HRID 1413990Notes

Reaction equation

HRID 1413990 reaction equation
[CH2:1](Cl)/[CH:2]=[CH:3]/[CH2:4]Cl.[C:7]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])(=[O:16])[CH2:8][C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:10]>>[CH:2]([CH:3]1[CH2:4][C:8]1([C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:10])[C:7]([O:17][CH2:18][CH2:19][CH2:20][CH3:21])=[O:16])=[CH2:1]

Participants

3

Reactant 2

HCID 136925Propanedioic acid, dibutyl esterHCID 6421971,4-Dichloro-2-butene, (2E)-

Product 1

HCID 20504385Di-n-butyl 2-vinylcyclopropane-1,1-dicarboxylateYield 69%

Procedure

Example 3 was repeated except the organic solvent was omitted and the mol ratio of trans 1,4-dichlorobutene-2 to di-n-butyl malonate was 2:1. Di-n-butyl 2-vinylcyclopropane-1,1-dicarboxylate was obtained in 69% yield.

Sources & evidence

ORD record
ord-c9c25e14317f4ae18ddda9b3b9197cac
Source dataset
uspto-grants-1981_02
Patent number
US04252739

Reaction notes

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