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ChemicalBook CAS DataBase List 4-METHOXY-3-HYDROXYACETOPHENONE
6100-74-9

4-METHOXY-3-HYDROXYACETOPHENONE synthesis

10synthesis methods
Preparation by saponification of 3-acetoxy-4-methoxy-acetophenone (90%) (59%).
-

Yield:6100-74-9 84% ,498-02-2 6% ,1131-62-0 4%

Reaction Conditions:

with lithium carbonate in N,N-dimethyl-formamide at 55; for 18 h;Inert atmosphere;chemoselective reaction;

Steps:

Methylation of 4-acyl-1,2-dihydroxybenzenes (9); General Procedure
General procedure: To a solution of the appropriate 4-acyl-1,2-dihydroxybenzene (9) (0.25 mol) and methyl iodide (71 g, 0.5 mol) in DMF (250 mL) was added Li2CO3, (37 g, 0.5 mol). The resulting suspension was stirred under argon at 55° C for 18 h. The reaction mixture was poured into water (1 L) containing conc. HCl (70 mL), extracted with ethyl acetate, chromatographed on silica gel (hexane/acetone, 20:1) to give products 10-12 and unreacted 4-acyl-1,2-dihydroxybenzenes (9).

References:

Khmelevskaya, Ekaterina A.;Pelageev, Dmitry N. [Tetrahedron Letters,2019,vol. 60,# 15,p. 1022 - 1024] Location in patent:supporting information

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