O[NH:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:5]=1[OH:11].S(Cl)(Cl)=O.C(N(CCCC)CCCC)CCC.[OH-].[Na+]>C(OC)(C)(C)C>[CH3:10][C:7]1[CH:8]=[CH:9][C:4]2[C:3]([OH:12])=[N:2][O:11][C:5]=2[CH:6]=1
50.0 g of N,2-dihydroxy-4-methylbenzamide was added to 350 mL of tert-butylmethylether, and 38.1 g of thionyl chloride was added dropwise at −1-0° C. This was stirred for 30 minutes at the same temperature. Then, 164 mL of tributylamine was added dropwise at −5-−3° C., and this was stirred for 1.5 hours at −5-5° C. To the reaction mixture, 200 mL of 20% sodium hydroxide aqueous solution was added, an organic layer was separated, and 100 mL of water, 42 mL of 20% sodium hydroxide aqueous solution and 5.0 g of celite were added. After insoluble matter was filtered off, the cake was washed with 100 mL of water. The filtrate and the washing solution were combined and an aqueous layer was separated. To the aqueous layer, 10 mL of acetone and 50 mL of acetic acid were added at 40-50° C. After stirring at the same temperature for 30 minutes, solids were filtered to obtain 40.1 g of 6-methyl-1,2-benzisoxazol-3-ol in the form of a pale yellow solid.
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