Hydrochloric Acid → 4'-(Octyloxy)-[1,1'-biphenyl]-4-carboxylic acid

Participants

Reaction Steps

n-Octyl bromide (1.63 mL) was added to a solution of 4-(4'-hydroxyphenyl)benzoic acid (2.02 g) and 5N sodium hydroxide (3.77 mL) in dimethylsulfoxide (25 mL) and the mixture was stirred at 60°-70° C. for a period of 18 hours. The reaction mixture was cooled to room temperature and then acidified with approximately 6 mL of 2N HCl and partitioned between ethyl acetate and water. The organic phase was washed with 3×250 mL of water and 1×250 mL brine and filtered. The filter cake was saved. The organic phase was dried over magnesium sulfate and the solvent was removed under reduced pressure to obtain the 4'-n-octyloxy[1,1'-biphenyl]-4-ylcarboxylic acid (1.54 g). The filter cake from above was washed with dichloromethane and traces of the organic solvent were removed under reduced pressure to yield 1.53 g of product. The material was combined to yield a total of 3.07 g of 4'-n-octyloxy[1,1'-biphenyl]-4-ylcarboxylic acid. 1H NMR (400 MHz, DMSO-d6) δ 0.87 (t, 3H), 1.29 (m, 8H), 1.41 (m, 2H), 1.72 (m, 2H), 4.01 (t, 2H), 7.03 (d, 2H), 7.68 (d, 2H), 7.73 (d, 2H), 7.98 (d, 2H).

Provenance & Evidence