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

HRID 54726

Reaction equation

HRID 54726 reaction equation
[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]

Participants

6

Reactant 4

HCID 1032Propionic AcidHCID 8471TriethylamineHCID 13586VinyloxiraneHCID 31263Propionic anhydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
125 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d4628cb5db4245138f2f75b0cd4d53b8
Source dataset
uspto-grants-1997_04
Patent number
US05623086

Linked notes

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