cas 15085-20-8, 2,3-Dihydro-7-methyl-1H-indene-4-carbonitrile | Articles data ｜lookchem

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15085-20-8

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Improved Synthesis of 3-Methylcholanthrene
An improved synthesis of 7-methylindan-4-yl 1-naphthyl ketone (3), an important precursor of 3-methylcholanthrene (1), has been developed.The key intermediates for 3, 4-cyano-7-methylindan (2a) and 4-(ethoxycarbonyl)-7-methylindan (2b), were conveniently prepared in high yields by reaction of 1-(1-pyrrolidino)cyclopentene (6) with sorbonitrile (5a) or ethyl sorbate (5b), followed by aromatization with sulfur. 1-Naphthylmagnesium bromide (4b) in the presence of cuprous iodide reacted cleanly with 4-(chloromethanoyl)-7-methylindan (12) to give 3.The Friedel-Crafts acylation of naphthalene with 12 afforded 84percent of 3 and 16percent of β isomer 13.Alternatively, 3 was prepared in 75percent yield by condensation of Grignard reagent 4b with 2a in THF.Thermal annelation of 3 afforded 1 in 41.5percent yield.
Tang, Ping Wah,Maggiulli, Cataldo A.
p. 3429 - 3432
(2007/10/02)

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Chemical Properties

Melting Point: 65-70°C
Boiling Point: 299.6°Cat760mmHg
Flash Point:135.4°C
Density: 1.07g/cm³
Storage Temp.:Refrigerator
Vapor Pressure: 0.00118mmHg at 25°C
PSA: 23.79000
LogP: 2.35538

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