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ChemicalBook CAS DataBase List Ethanone, 1-[3-(1-methylethyl)phenyl]- (9CI)
40428-87-3

Ethanone, 1-[3-(1-methylethyl)phenyl]- (9CI) synthesis

9synthesis methods
3-Bromocumene

5433-01-2

N-Methoxy-N-methylacetamide

78191-00-1

Ethanone, 1-[3-(1-methylethyl)phenyl]- (9CI)

40428-87-3

A THF solution (250 mL) of 1-bromo-3-(propan-2-yl)benzene (5.0 g, 25.11 mmol, 1.00 eq.) was added to a 500 mL round-bottomed flask protected by an inert N2 atmosphere. The reaction system was cooled to -60 °C and n-butyllithium (20 mL, 2.00 eq.) was slowly added dropwise under stirring. After the dropwise addition, stirring was continued at -60 °C for 30 min. Subsequently, the reaction system was warmed to -30 °C and N-methoxy-N-methylacetamide (3.9 g, 37.82 mmol, 1.50 eq.) was added slowly dropwise under stirring. After completion of the dropwise addition, the reaction mixture was continued to be stirred in a liquid nitrogen bath at -30 °C for 3 hours. At the end of the reaction, the reaction was quenched by adding 20 mL of water. The reaction mixture was diluted with 200 mL of ethyl acetate, washed sequentially with 2 x 100 mL of brine, and the organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:10) as eluent to give 2.7 g (66% yield) of the target product 1-(3-isopropylphenyl)ethanone as a colorless oil.

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Yield:40428-87-3 98%

Reaction Conditions:

with hydrogen;palladium on activated charcoal;5% Pd on active carbon in ethyl acetate;

References:

Abate, Agnese;Brenna, Elisabetta;Dei Negri, Claudia;Fuganti, Claudio;Serra, Stefano [Tetrahedron Asymmetry,2002,vol. 13,# 8,p. 899 - 904]