1-(4-Chlorophenyl)cyclopropanecarboxylic acid

White crystalline powder

The cyclopropanecarbonitrile ( 18 gm) obtained in was added to 20percent sulfuric acid (184ml). The temperature of the reaction mass was slowly raised and maintained at reflux for 10-12 hours. After 12 hours , ethyl acetate was used to extract the product. The acid product from the organic layer was then extracted into 20percent NaOH solution. The aqueous layer was then acidified to pH 2-4 with concentrated HCl. The white solid product obtained was filtered and washed with water. The product p- chlorophenylcyclopropanecarboxylic acid was dried. The yield was 90-95percent and the product had apurity of 99.4percent by HPLC. The melting point was 152-155A stirred solution of 1-(4-chlorophenyl)cyclopropane-1-carbonitrile (step 1, 30.0 g, 169.49 mmol, 1.0 eq), sodium hydroxide (20.3 g, 508.47 mmol, 3.0 eq), diethylene glycol(120 ml) and water (35.4 ml) was refluxed for about 18 hours. TLC indicated startingmaterial was consumed and the desired product was observed. The reaction mixture was poured into water (1800 ml) and acidified to pH4.0 with concentrated HC1 (54 ml). The generated crystals were collected by filtration and dried under vacuum to obtain the desired product (30.0 g, 90.3percent yield) as a pale-brown colour solid. ‘H NMR (300 MHz, DMSO-d6):ppm 12.40 (br.s., 1H), 7.34 (m, 4H), 1.48-1.42 (m, 2H), 1.16-1.10 (m, 2H).350 ml rauchende Salpetersure werden bei -25 bis -30C portionsweise mit 50.0 g (0.21 Mol) 1-(4-Chlor-phenyl)-cyclopropancarbonsure versetzt. Nach beendeter Zugabe wird noch 15 Minuten bei -25C gerhrt und anschlieend auf Eis gegossen. Die ausgefallene Substanz wird abgesaugt, mit Wasser gewaschen und getrocknet. Ausbeute: 58.5 g (95 % der Theorie), Rf-Wert: 0.43 (Kieselgel; Methylenchlorid/Methanol = 9.5:0.5)e. 1-(4-Chloro-3-nitrophenyl)-cyclopropanecarboxylic acid 350 ml fuming nitric acid are combined batchwise at -25 to -30 C. with 50.0 g (0.21 mol) of 1-(4-chloro-phenyl)-cyclopropanecarboxylic acid. After it has all been added the mixture is stirred for a further 15 minutes at -25 C. and then poured onto ice. The substance precipitated is suction filtered, washed with water and dried. Yield: 58.5 g (95% of theory), Rf value: 0.43 (silica gel; methylene chloride/methanol=9.5:0.5);Step 1): Compound 51 (7.0 g, 35.7 mmol) was added to 50 mL of fuming nitric acid in batches at -30 C. After the addition, the mixture was stirred at -30 C for 15 min.The reaction solution was slowly poured into 100 mL of ice water, filtered, and dried to obtain 8.0 g of the product as a yellow solid (Compound 52).

Molecular Weight:196.63
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:196.0291072
Monoisotopic Mass:196.0291072
Topological Polar Surface Area:37.3
Heavy Atom Count:13
Complexity:215
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes