1-(4-METHYLPHENYL)-1-CYCLOPENTANECARBONITRILE synthesis

Yield:68983-70-0 68%

Reaction Conditions:

Stage #1: (4-methylphenyl)acetonitrilewith sodium hydroxide in N,N-dimethyl-formamide; for 0.5 h;
Stage #2: 1,4-dibromo-butane in N,N-dimethyl-formamide at 70 - 75; for 4 h;

Steps:

Nitriles 1a-1c. General method.

General procedure: To solution of 19.6 g (0.1 mol) of 4-methylbenzyl cyanide in 100 mL of anhydrous DMF under stirring was added 8 g (0.3 mol) of NaOH powder, after 30 min 0.1 mol of dihaloalkane (dibromobutane or dichlorodiethyl ether) was added at a rate maintaining the reaction temperature no higher than 70-75°C (at the preparation of compound 1 0.3 mol of MeI was added and the temperature of the mixture was maintained no higher than 40°C), and the mixture was stirred at this temperature for 4 h. After cooling the mixture was diluted with 100 mL of benzene and 200 mL of water, the organic layer was separated, the aqueous layer was twice extracted with benzene. The combined benzene extracts were washed with water, dried with MgSO₄, the solvent was distilled off, the residue was distilled in a vacuum.

References:

Aghekyan;Mkryan;Tsatinyan;Noravyan;Gasparyan [Russian Journal of Organic Chemistry,2016,vol. 52,# 2,p. 209 - 213][Zh. Org. Khim.,2016,vol. 52,# 2,p. 226 - 230,5]