Methyl 2-(4-cyanophenyl)-2-methylpropanoate synthesis
- Product Name:Methyl 2-(4-cyanophenyl)-2-methylpropanoate
- CAS Number:444807-47-0
- Molecular formula:C12H13NO2
- Molecular Weight:203.24
Yield:444807-47-0 98%
Reaction Conditions:
with sodium hydride in N,N-dimethyl-formamide at 0 - 35; for 2 h;
Steps:
12 Methyl 4-cyano-α,α-dimethylbenzeneacetate
To a solution of methyl 4-cyanobenzeneacetate (2.646 g, 15.1 mmol) and iodomethane (2.4 ml) in N,N-dimethylformamide (50 ml) was slowly added 60% oily sodium hydride (1.55 g, 38.8 mmol) under ice-cooling. The reaction mixture was stirred for 2 hours at room temperature. The reaction solution was slowly added to ice water, and extracted with ethyl acetate. The extracts were washed with a saturated aqueous solution of sodium chloride, dried, and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography (ethyl acetate/hexane 3:1) to give the title compound (2.996 g, yield 98%). 1H NMR (CDCl3) δ 1.59 (6H, s), 3.67 (3H, s), 7.42-7.47 (2H, m), 7.61-7.65 (2H, m).
References:
EP1541576,2005,A1 Location in patent:Page/Page column 41
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