Hydroxyamine hydrochloride → 2-Hydroxy-3-bromo-5-(1,1-dimethylethyl)benzaldehyde oxime

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Reaction Steps

A mixture of 12.86 g (50.0 mmol) of 2-hydroxy-3-bromo-5-(1,1-dimethylethyl)benzaldehyde (see L. C. Felton and J. H. Brewer, Science, 105:409 (1947) as an example of how to obtain this material) and 3.82 g (55.0 mmol) of hydroxylamine hydrochloride in 30 ml of ethanol, 30 ml of water and 30 ml of tetrahydrofuran was cooled in an ice-water bath. Sodium bicarbonate (5.04 g, 60.0 mmol) was added in small portions over 15 minutes. After stirring for 1 hour at ambient temperature, water (200 ml) was added and the solid was filtered and dried. There was obtained 13.2 g (78.5 mmol, 97%) of 2-hydroxy-3-bromo-5-(1,1-dimethylethyl)benzaldehyde oxime as a white solid; mp 167.5°-168° C.

Provenance & Evidence