Hydrochloric Acid → 4'-(1-Methyl-heptyloxy)-4-biphenylcarboxylic acid

Participants

Reaction Steps

Preparation of optically active p-(1-methylheptyloxy)benzoic acid 4'-bromo-4-biphenylyl ester (a compound of the formula (I) wherein l=1, m=1, R=C6H13, X=Br and Y, Z=H; Sample No. 9) P-hydroxybenzoic acid methyl ester (IV) (28.5 g, 0.187 mol) was dissolved in methanol (120 ml), and KOH (10.1 g, 0.187 mol) was added to and dissolved in the solution, followed by adding to the resulting solution, optically active p-toluenesulfonic acid 1-methyl-heptyl ester (III) (58.6 g, 0.206 mol) obtained in Example 1, keeping the mixture under reflux for 4 hours, then cooling, adding toluene (200 ml) and 6N--HCl (50 ml), washing the resulting toluene layer with 2N--NaOH aqueous solution and then with water till the washing water became neutral and distilling off toluene to obtain as a residue, optically active p-(1-methyl-heptyloxy)benzoic acid methyl ester (V) (14.2 g). This ester (14.2 g, 0.054 mol) was dissolved together with ethanol (5 ml), NaOH (3.2 g, 0.081 mol) and water (20 ml), followed by heating the solution under reflux for one hour, then cooling, pouring the reaction fluid in 6N--HCl aqueous solution (50 ml) with stirring, filtering off deposited crysrals and recrystallizing from ethanol to obtain optically active p-(1-methyl-butyloxy)benzoic acid (VI) (8.1 g) having a melting point of 61.2°~63.1° C. To this product (7.5 g, 0.030 mol) was added thionyl chloride (6.0 g, 0.047 mol), followed by heating the mixture under reflux for one hour, and distilling off excess thionyl chloride to obtain opticaly active p-(1-methyl-heptyloxy)benzoic acid chloride (VII) (5.8 g).

Provenance & Evidence