2-Methylbenzaldehyde → [C(E)]-2-Methylbenzaldehyde oxime

Temperature

0 °C

A solution of sodium hydroxide (2.00 g, 50.0 mmol, 1.19 equiv) in water (25 mL) was added to a stirred solution of hydroxylamine hydrochloride (3.30 g, 47.8 mmol, 1.15 equiv) in water (25 mL) at 0° C. The resulting solution was stirred for 10 min at 0° C. Then a solution of 2-methylbenzaldehyde (5.00 g, 41.6 mmol, 1.00 equiv) in ethanol (25 mL) was added slowly over 5.0 min. The resulting solution was allowed to stir for an additional 1 h at RT. The solution was diluted with H2O (100 mL), extracted with ethyl acetate (120 mL) and the organic layers were combined, washed with brine (100 mL), dried over magnesium sulfate and concentrated under vacuum to give (E)-2-methylbenzaldehyde oxime as an off-white crystalline solid. MS m/z 136.0 (M+1).

1. stirringto stir for an additional 1 h at RT
2. extractionextracted with ethyl acetate (120 mL)
3. washwashed with brine (100 mL)
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated under vacuum

ORD record

ord-8ab2cc6d4ebe4fc984c79c2082a29203

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150568B2