Propionic Acid → 3,4-Dipropionyloxy-1-butene

HRID 54726

반응식

HRID 54726 반응식
[C:1]([O:5][C:6](=O)[CH2:7][CH3:8])(=[O:4])[CH2:2][CH3:3].[CH2:10](N(CC)CC)C.[C:17]([OH:21])(=[O:20])[CH2:18][CH3:19].O1CC1C=C>COCCOCCOC>[C:17]([O:21][CH:7]([CH2:6][O:5][C:1](=[O:4])[CH2:2][CH3:3])[CH:8]=[CH2:10])(=[O:20])[CH2:18][CH3:19]

참가 물질

6

반응물 4

HCID 1032Propionic AcidHCID 8471TriethylamineHCID 13586VinyloxiraneHCID 31263Propionic anhydride

생성물 1

HCID 212251023,4-Dipropionyloxy-1-butene수율 90%

시약·촉매·용매 1

HCID 8150Diglyme용매

반응 조건

온도
125 °C

실험 절차

A 100-mL autoclave was charged with 57.2 g (0.44 mol) propionic anhydride, 1.62 g (0.016 mol) of triethylamine, 1.2 g (0.016 mol) of propionic acid and 3.44 g of diglyme. The autoclave was purged with helium twice, then the vessel was pressurized to 6.2 bars (75 psig) with helium followed by agitation. The reaction mixture was heated to 125° C., then 31.35 mL (0.40 mol) of 3,4-epoxy-1-butene was introduced to the reactor via syringe pump over 10 seconds. A first sample was taken at 1 min, then sequential samples were obtained every 15 min during the course of 2 hrs for analysis by GC. GC analysis of the crude mixture after 2 hrs revealed a 90% yield of 3,4-dipropionyloxy-1-butene with a 91% selectivity and 6% 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 0.017 min-1 (Table A). This example shows the use of another carboxylic anhydride with its conjugate carboxylic acid.

후처리

  1. customThe autoclave was purged with helium twice
  2. customsequential samples were obtained every 15 min during the course of 2 hrs for analysis by GC

출처 및 근거

ORD 기록
ord-d4628cb5db4245138f2f75b0cd4d53b8
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05623086

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