氢氧化钠氯气,碘仿反应.docVIP

Org. Synth. 1937, 17, 65 β-NAPHTHOIC ACID [2-Naphthoic acid] Submitted by M. S. Newman and H. L. Holmes. Checked by W. W. Hartman and F. W. Jones. 1. Procedure In a 3-l. flask is placed a solution of 184 g. 4.6 moles of sodium hydroxide in 300–400 cc. of water; sufficient ice is added to make the total volume about 1.5 l. Chlorine is passed into the solution, the temperature being kept below 0° by means of a salt-ice bath, until the solution is neutral to litmus, then a solution of 34 g. of sodium hydroxide in 50 cc. of water is added Note 1 and Note 2 . The flask is now supported by a clamp and equipped with a thermometer and an efficient stirrer. The solution is warmed to 55°, and 85 g. 0.5 mole of methyl β-naphthyl ketone Note 3 is added. The mixture is vigorously stirred, and, after the exothermic reaction commences, the temperature is kept at 60–70° Note 4 by frequent cooling in an ice bath until the temperature no longer tends to rise. This requires thirty to forty minutes. The solution is stirred for thirty minutes longer and then the excess hypochlorite is destroyed by adding a solution of 50 g. of sodium bisulfite in 200 cc. of water Note 5 . After cooling to room temperature, the reaction mixture is transferred to a 4-l. beaker and carefully acidified with 200 cc. of concentrated hydrochloric acid. The crude colorless acid is collected on a Büchner funnel, washed with water, and sucked as dry as possible with a rubber dam. After drying, the acid is crystallized Note 6 from 600 cc. of 95 per cent alcohol, giving 75–76 g. 87–88 per cent of the theoretical amount of β-naphthoic acid melting at 184–185° corr. . By distilling 450 cc. of solvent from the mother liquor, an additional 9 g. 10 per cent of the theoretical amount of acid, m.p. 181–183° corr. , is obtained Note 7 . 2. Notes 1. It is reported that, in preparing a sodium hypochlorite solution by passing chlorine into sodium hydroxide, it is very difficult to determine the neutral po