Acetone → (3E)-4-(2,6-Dichlorophenyl)-3-buten-2-one

Temperature

0 °C

A round bottom flask equipped with magnetic stirrer and nitrogen inlet was charged with 2,6-dichlorobenzaldehyde (5.0 g, 28.57 mmol), acetone (42 ml, 0.571 mol) and water (20 ml). The mixture was cooled to 0° C. and a solution of sodium hydroxide (1.14 g, 28.57 mmol) in water (20 ml) was added drop wise during 1 hour to the vigorous stirred suspension. The reaction mixture was stirred for an additional 0.5 hour. The reaction mixture was concentrated in vacuo, poured onto 10% HCl (100 ml) and extracted with ethyl acetate (3×50 ml). Combined organic layers were dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by flash chromatography over silica gel (350 g) (eluent: n-hexane/ethyl acetate 10:1) to afford 6.0 g (97% of theory) of (E)-4-(2,6-dichloro-phenyl)-but-3-en-2-one in form of a pale yellow oil.

1. customA round bottom flask equipped with magnetic stirrer and nitrogen inlet
2. concentrationThe reaction mixture was concentrated in vacuo
3. additionpoured onto 10% HCl (100 ml)
4. extractionextracted with ethyl acetate (3×50 ml)
5. dry with materialCombined organic layers were dried over anhydrous sodium sulfate
6. customThe solvent was removed in vacuo
7. customthe residue was purified by flash chromatography over silica gel (350 g) (eluent: n-hexane/ethyl acetate 10:1)

ORD record

ord-9d3b6ac7b2d64fa6a302af5a7cf639ef

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08357635B2