Acetic Acid → 3,4-Diacetoxy-1-butene

HRID 54728

反応式

HRID 54728 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: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]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 13586Vinyloxirane2 回

生成物 1

HCID 27350013,4-Diacetoxy-1-butene収率 96%

試薬・触媒・溶媒 1

HCID 8150Diglyme溶媒

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, 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).

後処理

  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

出典と根拠

ORDレコード
ord-ca47668524a7466ebbc86aa56b1ea08f
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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