Ethyl Acetate → HCID 13840699, compound

Temperature

0 °C

To a solution of 4-chloromethylbenzoyl chloride (40 g) in tetrahydrofuran (400 ml) was added dropwise methylmagnesium bromide (3M, tetrahydrofuran solution) (70 ml) under ice-cooling and the mixture was stirred at 0° C. for 4 hr. The reaction mixture was poured into an aqueous ammonium chloride solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate and the solvent was evaporated to give a yellow oil. The oil was subjected to silica gel column chromatography (developing solvent; hexane:ethyl acetate=9:1) to give an orange oil. The oil was subjected to silica gel column chromatography (developing solvent; hexane:ethyl acetate=4:1) to give the title compound (10 g) as a pale-brown oil, m.p.=101-103° C.

1. temperaturecooling
2. extractionextracted with ethyl acetate
3. washThe extract was washed with saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. customthe solvent was evaporated
6. customto give a yellow oil
7. customto give an orange oil

ORD record

ord-1ba427fec17e4bfbb0e359a38daa504d

Source dataset

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06455528B1