A NEW ALDEHYDE SYNTHESIS via DIMETHYLAMIDES 1089 ~* O D 1.4042, and 2.5 g., 8.57, yield, of capronitrile, b . p . 73" a t 53-55 m m . , n z O~ 1,4070.C. Cyclohexanecarbonitrile.-Cyclohexanecarboxaldehyde, b.p. 63-66" a t 23-24 mm., n % 1.4507, was obtained in 71y0 yield.D . Benzonitri1e.-Benzaldehyde, b . p . 81-82' a t 31 mm., RZoD 1.5452, was obtained in 767? yield. E. p-Chlorobenzonitri1e.-Lithium triethoxyaluminohydride (0.238 mole) was prepared in 238 ml. of ether. Into this stirred solution was added 32.7 g . (0.238 mole) of p-chlorobenzonitrile all a t once a t ice-bath temperature. The reaction mixture was hydrolyzed, after an hour, with 200 ml. of 5 i V sulfuric acid.Ether was distilled and the resulting aqueous layer was steam distilled. p-Chlorobenzaldehyde, m . p . 47-47.5', was obtained (27.9 g , ) i n 8 3 . 5 ( 2 yield. Recrystallization from hot water did not change the m.p.Reduction with Lithium Tri-n-butoxyaluminohydride on a Preparative Scale .-The use of lithium tri-n-butoxyaluminohyiride is useful in cases where t h e removal of ethyl alcohol from the product offers difficulties.Cyclopropanecarbonitrile. -In a 1-1 ., three-necked, round-bottom flask equipped with a condenser, dropping funnel, and stirrer, flushed with nitrogen, was placed 0.3 mole of lithium aluminum hydride in 300 ml. of ether ( 1 M solution). T o this solution was added dropwise over a period of 75 min., 0.9 mole (66.6 9 . ) of 1butanol, maintaining the temperature a t -10 to -5 " . The reaction was stirred for another 15 min. T o this solution ( -10") was added 20.1 g . (0.3 mole) of cyclopropanecarbonitrile over 15 min., the temperature rising t o 8 " . The reaction was stirred for 1 h r . a t 3" (ice b a t h ) and then decomposed by 300 ml. of 5 AY sulfuric acid. The ether layer was separated and the heterogen-eous aqueous layer was extracted three times with 25-ml. portions of ether. T h e combined ether extracts were washed with sodium bicarbonate solution and water and then dried over sodium sul-