On hydrolysis of the two above substances with 50% alcoholic 0.5 N potassium hydroxide, the known 5nitro resorcinol, m. p. 157-159°, was isolated in the usual manner and gave, on methylation, the known 3,5-methoxynitrobenzene, m. p. 89.5°.On dissolving 0.5 g. of pentaacetyl-nitrodesoxyinositol III, as described under (11), in 5 cc. of hot pyridine, it was transformed almost quantitatively into diacetyl-5-nitroresorcinol.
Since acetylketene, in conjunction with its resonance isomer /3-crotonolactone, is the struc-ture1 of the dimer of ketene it seemed reasonable to think that acetoacetyl chloride could be synthesized from it by reaction with hydrogen chloride. Such proved to be the case.CHgCOCH=CO + HC1 -> CH3COCH2COClIn the present synthesis low temperatures were found to be necessary because of the instability of acetoacetyl chloride at temperatures above -
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