Potassium Hydroxide → Di-n-butyl 2-vinylcyclopropane-1,1-dicarboxylate

HRID 1413989Notes

Reaction equation

HRID 1413989 reaction equation
[OH-].[K+].[CH2:3](Cl)/[CH:4]=[CH:5]/[CH2:6]Cl.[C:9]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])(=[O:18])[CH2:10][C:11]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:12]>[Cl-].C(C([NH3+])(C(=O)CCCCCCC)C(=O)CCCCCCC)(=O)CCCCCCC>[CH:4]([CH:5]1[CH2:6][C:10]1([C:11]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:12])[C:9]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:18])=[CH2:3]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 136925Propanedioic acid, dibutyl esterHCID 6421971,4-Dichloro-2-butene, (2E)-

Product 1

HCID 20504385Di-n-butyl 2-vinylcyclopropane-1,1-dicarboxylateYield 37.1%

Reagents, catalysts & solvents 1

HCID 77620884Tricaprylylmethyl ammonium chlorideCatalyst

Procedure

Employing a reaction similar to that described in Example 1 except that a hydrocarbon solvent is included in the reaction mixture, 152 g 50% aqueous potassium hydroxide solution was added dropwise to a vigorously stirred solution of 64.5 g (0.52 mol) trans 1,4-dichlorobutene-2,112.5 g (0.52 mol) di-n-butyl malonate, 4.0 g tricaprylylmethylammonium chloride and 200 cc petroleum ether. Upon workup and distillation, 47.6 g (37.1% yield) of di-n-butyl 2-vinylcyclopropane-1,1-dicarboxylate (bp 101°-104° C. (0.30 mm)); nD24° 1.4556) was obtained. Infrared and proton nmr spectra were consistent with th desired vinylcyclopropane product. Attempts to carry out the reaction in the absence of the onium compound were unsuccessful.

Workup

  1. customa reaction similar to

Sources & evidence

ORD record
ord-2a65ee42e4704d9fafdb340c59fa6447
Source dataset
uspto-grants-1981_02
Patent number
US04252739

Reaction notes

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