Acetic Acid → 3-Acetylpyridine
Reaction equation
[C:1]([O:9]CCCC)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.O.[C:15](O)(=O)C>>[C:1]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)(=[O:9])[CH3:15]Participants
Procedure
A tubular reactor with an i. d. of 23.5 mm was filled with 270 ml (≈227 g) of catalyst from example 1. A mixture of butyl nicotinate (30 g/h), water (54 g/h) and acetic acid (210 g/h) was fed over an evaporator using a metering pump to the tubular reactor heated by a salt bath. A small flow of nitrogen (1 l/h) guaranteed the transport of the vapours. The temperature of the bath was 410° C. The reaction vapours were condensed in an aqueous circulation system. After a total running time of 35 h, the reaction solution was collected. A portion of this solution corresponding to a total of 710 g of butyl nicotinate was worked up to isolate the product. 81% of butyl nicotinate was converted to give 293 g of 3-acetyl-pyridine, corresponding to a selectivity of 75% and a yield of 61%. The selectivity of pyridine formation was 4%.
Workup
- customwas fed over an evaporator
- temperatureheated by a salt bath
- customwas 410° C
- customThe reaction vapours
- customcondensed in an aqueous circulation system
- customAfter a total running time of 35 h, the reaction solution was collected
- customto isolate the product
Sources & evidence
- ORD record
- ord-0cb5277234c64044be1ee68c95c66568
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07067673B2
Reaction notes
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