Oxygen → 2-Chlorobenzoic Acid

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Cl[C:2]1C=C[CH:5]=[CH:4][C:3]=1C.[CH2:9]([CH:11]1[O:13][CH2:12]1)[Cl:10].[O:14]=O>CCCCC(C([O-])=O)CC.CCCCC(C([O-])=O)CC.[Co+2]>[Cl:10][C:9]1[CH:5]=[CH:4][CH:3]=[CH:2][C:11]=1[C:12]([OH:13])=[O:14]

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온도: 155 °C

실험 절차

Into the column described in Example 1 were charged 453 grams (3.58 moles) of o-chlorotoluene, 2.25 grams of cobalt octoate (6% Co), and 2.25 grams of epichlorohydrin. The reaction mixture was heated to 155° C. and maintained at that temperature while oxygen that had been sparged through epichlorohydrin was bubbled through it at the rate of 200 ml./min. Throughout the reaction period, the gases leaving the reactor remained non-acidic. At the end of 23 hours, the reaction mixture was removed from the column, cooled to 75° C., and extracted with 600 grams of 10 percent aqueous sodium hydroxide solution. The layers that formed were separated. The aqueous layer was diluted with water to a volume of 1500 ml. and then acidified with hydrochloric acid. The o-chlorobenzoic acid that precipitated was collected, washed with water, and dried. There was obtained 180 grams (1.155 moles) of o-chlorobenzoic acid. The conversion of o-chlorotoluene to o-chlorobenzoic acid was 14 percent. The yield of o-chlorobenzoic acid, based on o-chlorotoluene reacted, was 78.6 percent.