Propanal → (2E)-2-Methyl-3-(3-methylphenyl)-2-propenal

A solution of potassium hydroxide (24 g, 0.36 mol, 0.6 eq, with a purity of 85%) in ethylene glycol (120 g) and water (12 g) was charged into a 500 mL three-necked round-bottom flask equipped with a reflux condenser and a mechanical stirrer. 3-methyl benzaldehyde (70 g, 0.59 mol) was added dropwise. The stirred reaction mixture was heated at 38-42° C. and propionaldehyde (41 g, 0.71 mol, 1.2 eq) was dosed in over 3.25 h. After a further hour at 40° C., the reaction mixture was cooled to ambient temperature and the two layers separated. The organic layer thus obtained was washed with water (2×100 mL), dried over magnesium sulphate and concentrated. The resulting crude product was distilled via a Vigreux column (1.0 mBar, 87-92° C.), to give (2E)-2-methyl-3-(3-methylphenyl)acrylaldehyde (65.9 g, gc purity>95%; yield 70%).

1. customequipped with a reflux condenser and a mechanical stirrer
2. customThe stirred reaction mixture
3. customwas dosed in over 3.25 h
4. waitAfter a further hour at 40° C.
5. temperaturethe reaction mixture was cooled to ambient temperature
6. customthe two layers separated
7. customThe organic layer thus obtained
8. washwas washed with water (2×100 mL)
9. dry with materialdried over magnesium sulphate
10. concentrationconcentrated
11. distillationThe resulting crude product was distilled via a Vigreux column (1.0 mBar, 87-92° C.)

ORD 기록

ord-7d5d6fe7d1724e9483a2d243a78968a6

출처 데이터셋

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08709994B2