PRODUCTION OF 4-(NITROPHENOXY)-3-METHYL-1-BUTEN-3-OL

摘要

PROBLEM TO BE SOLVED: To obtain the subject compound useful as a synthetic intermediate of a chroman derivative as a blood sugar reducing agent at a high yield by reacting methylbutenediol with a halogenonitrobenzene in the presence of a base. SOLUTION: This 4-(nitrophenoxy)-3-methyl-1-buten-3-ol expressed by formula II is obtained by reacting 1 mol of 3-methyl-1-butene-3,4-diol with 0.5-2 mol of a halogenonitrobenzene expressed by formula I (X is a halogen) in the presence of preferably 1-3 mol of a base (e.g. an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide; an alkaline earth metal hydroxide such as calcium hydroxide or magnesium hydroxide) and in the presence or absence of a solvent (e.g. an aromatic hydrocarbon such as toluene or xylene; an ether such as tetrahydrofuran or diethyl ether; N,N-dimethylformamide) at 20-50 deg.C for 1-5 hrs.