Sodium Hydroxide → 1H-Indene-5-carbonitrile, 2,3-dihydro-1,1,2,3,3,6-hexamethyl-

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Reaction Steps

The crude product from Step III was dissolved in 250 ml. of benzene in a 50-ml. flask equipped with mechanical stirrer, cooling bath, thermometer, addition funnel, condenser, and static nitrogen head. Thionyl chloride (72 ml.) was added gradually with cooling over six mimutes at 24° to 30° C. The mixture was then heated to reflux for about 4 hours, and after cooling, 150 ml. of 5% sodium hydroxide solution was added at between 32° and 50° C., with cooling, over 16 minutes. The entire contents of the reaction flask were transferred to a separatory funnel and washed twice with 500 ml. of 5% sodium hydroxide solution. The washings were extracted in succession with 50 ml. of benzene. The organic phases were combined and flash evaporated on a rotary evaporator for one hour at 50° C. 10 mm. Hg to yiedl 30.6 g. of crude nitrile. The infrared spectrum (mineral oil mull) showed a medium intensity nitrile band at 2400 cm-1. The crude nitrile was taken up in 100 ml. of benzene and run onto a 1 1/8 inch by 35 inch chromatography column (wet-packed with 400 g. of MCB grade 923 silica gel using benzene as packing solvent). Pure nitrile was collected after 525 ml. of benzene were eluted from the column. A 5 g. portion of the chromatographed nitrile was recrystallized from hexane. The recrystallized nitrile was dissolved in 30 ml. of methanol, 2 g. of Draco K-9 activated carbon added, and the slurry filtered. After repeating the carbon treatment, the product was again recrystallized from hexane. The recrystallized product melted at 70.2° to 72.8° C. NMR spectrum (CDCl3 with TMS reference):

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