Acetic Acid → 3,4-Diacetoxy-1-butene

HRID 54728

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HRID 54728 반응식
[O:1]1[CH2:5][CH:2]1[CH:3]=[CH2:4].[C:6]([O:9]C(=O)C)(=[O:8])[CH3:7].C(N(CC)CC)C.[C:20](O)(=[O:22])[CH3:21]>COCCOCCOC>[C:6]([O:9][CH:2]([CH2:5][O:1][C:20](=[O:22])[CH3:21])[CH:3]=[CH2:4])(=[O:8])[CH3:7]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 13586Vinyloxirane2회

생성물 1

HCID 27350013,4-Diacetoxy-1-butene수율 96%

시약·촉매·용매 1

HCID 8150Diglyme용매

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온도
125 °C

실험 절차

A 300-mL autoclave was charged with 40 mL (0.50 mol) of 3,4-epoxy-1-butene, 56.2 g (0.55 mol) acetic anhydride, 2.0 g (0.02 mol ) of triethylamine, 3.6 g (0.06 mol) acetic acid and 4.2 mL of diglyme. The autoclave was purged with nitrogen twice, then the vessel was pressurized to 8 bars (100 psig) with nitrogen. The agitator was started and an initial sample was taken. Then the mixture was heated to 125° C. During the course of 2.5 hrs, samples were obtained every 15 min for analysis by GC. GC analysis of the crude mixture after 2.5 hrs revealed a 96% yield of 3,4-diacetoxy-1-butene and 1.4% 3,4-epoxy-1-butene. The reaction was observed to be first order in 3,4-epoxy-1-butene with a first order rate constant of 0.037 min-1 (Table A). This example demonstrates the catalytic effect of a tertiary amine with three molar equivalents of acetic acid (Table B).

후처리

  1. customThe autoclave was purged with nitrogen twice
  2. customDuring the course of 2.5 hrs, samples were obtained every 15 min for analysis by GC

출처 및 근거

ORD 기록
ord-ca47668524a7466ebbc86aa56b1ea08f
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05623086

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