Methanol → 2-Methyl-2-oxazoline

Participants

Reaction Steps

A 127.6 g portion (1.5 moles) of 2-methyl-2-oxazoline is mixed with 192.0 g (6.0 moles) absolute methanol and 11.4 g (0.3 mole) lithium methoxide in a one-liter stainless steel Parr reactor equipped with a turbine stirrer. The reactor is sealed and heated, with stirring, to between 160° C and 165° C and 220 psig. The reaction is continued under those conditions for a period of 23.5 hours. Samples are periodically taken from the reactor through a dip-pipe which is below the liquid level. Analysis of these samples by gas chromatography with an internal standard indicates that, at 60-75 percent oxazoline conversions, corresponding amide yields are very high (95-100 percent) based upon the amount of oxazoline converted. At higher oxazoline conversions, a significant by-product appears, which is identified as 2-methoxyethylamine. The concentration of this amine levels out, and at 96.4 percent methyl oxazoline conversion, an 82.3 percent yield of 2-methoxyethylacetamide and an 11 percent yield of 2-methoxyethylamine results. Thus, yields of amide and amine, based on a 96.4 percent oxazoline conversion, are 93.3 percent.

Provenance & Evidence