Benzene → Diethyl 2-vinylcyclopropane-1,1-dicarboxylate

HRID 1065031노트

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HRID 1065031 반응식
[CH2:1](Cl)/[CH:2]=[CH:3]/[CH2:4]Cl.C([C:9](CC)([C:13]([O-:15])=[O:14])[C:10]([O-:12])=[O:11])C.[CH:18]1C=CC=C[CH:19]=1.[CH2:24]1CC2OCCOCCOC3C(OCCOCCOC2C[CH2:25]1)CCCC3>>[CH:2]([CH:3]1[CH2:4][C:9]1([C:13]([O:15][CH2:24][CH3:25])=[O:14])[C:10]([O:12][CH2:18][CH3:19])=[O:11])=[CH2:1]

참가 물질

5

반응물 4

HCID 241BenzeneHCID 85955Dicyclohexano-18-crown-6HCID 6421971,4-Dichloro-2-butene, (2E)-HCID 69515632,2-Diethylpropanedioate2회

생성물 1

HCID 111025Diethyl 2-vinylcyclopropane-1,1-dicarboxylate수율 61%

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온도
83 °C

실험 절차

Employing a procedure similar to that described in Example I, 6.25 gms (0.05 mol) 1,4-dichlorobutene-2 and 8 gms (0.05 mol) diethylmalonate were condensed. The reaction was carried out in 50 mls benzene using 0.11 mol potassium hydroxide and 5 mol percent, based on the diethylmalonate, catalyst (dicyclohexano-18-crown-6). After the reactants were combined and the mild exotherm subsided, the reaction mixture was heated for about 4 hours to a maximum temperature of 83° C. Approximately 4 mls water was removed during the course of the reaction. Upon workup of the reaction mixture, 9.23 gms very light yellow-orange oil was recovered. Vacuum distillation of the crude product yielded pure diethyl 2-vinylcyclopropane-1,1-dicarboxylate in 61% yield. The distillation residue (1.52 gms), consisting primarily of dicyclohexano-18-crown-6, was retained for reuse.

후처리

  1. customcondensed
  2. customApproximately 4 mls water was removed during the course of the reaction
  3. customUpon workup of the reaction mixture, 9.23 gms very light yellow-orange oil was recovered
  4. distillationVacuum distillation of the crude product

출처 및 근거

ORD 기록
ord-cb49062e08ba4176b844f23899f0296b
출처 데이터셋
uspto-grants-1982_05
특허 번호
US04328168

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