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

HRID 54722

反応式

HRID 54722 の反応式
[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]

参加物

5

反応物 4

HCID 7918Acetic AnhydrideHCID 8150DiglymeHCID 8471TriethylamineHCID 13586Vinyloxirane

生成物 1

HCID 27350013,4-Diacetoxy-1-butene収率 92%

反応条件

温度
125 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-6e6ef29129cb420f913406ea274eb835
出典データセット
uspto-grants-1997_04
特許番号
US05623086

関連ノート

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