Acetic Anhydride → 3,4-Diacetoxy-1-butene

HRID 54722

반응식

HRID 54722 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[O:21][CH2:22][CH2:23]OCCOC>>[C:6]([O:9][CH:2]([CH2:5][O:1][C:22](=[O:21])[CH3:23])[CH:3]=[CH2:4])(=[O:8])[CH3:7]

참가 물질

5

반응물 4

HCID 7918Acetic AnhydrideHCID 8150DiglymeHCID 8471TriethylamineHCID 13586Vinyloxirane

생성물 1

HCID 27350013,4-Diacetoxy-1-butene수율 92%

반응 조건

온도
125 °C

실험 절차

A 300-mL autoclave was charged with 40 mL (0.50 mol) of 3,4-epoxy-1-butene, 63.2 g (0.62 mol) acetic anhydride, 4.06 g (0.041 mol) of triethylamine 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. The mixture was heated to 125° C. During the course of 2.5 hrs, samples were taken every 15 min for analysis by GC. GC analysis of the crude mixture after 2.5 hrs revealed a 92% yield of 3,4-diacetoxy-1-butene with a 92% selectivity and 0.36% 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 the tertiary amine alone.

후처리

  1. customThe autoclave was purged with nitrogen twice
  2. waitGC analysis of the crude mixture after 2.5 hrs revealed

출처 및 근거

ORD 기록
ord-6e6ef29129cb420f913406ea274eb835
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05623086

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