3- Methoxy-4-hydroxyacetophenone

After 72 h at room temperature with a substrate catalyst ratio (R) of 10, the reaction mixture was methylated with dimethylsulphate and potassium carbonate and analyzed by GLC-MS. Veratric acid methyl ester 4 and 1,2-dimethoxybenzene 22 were recognized, indicating that the oxidation reaction mixture contained vanillic acid methyl ester 6 and ortho-methoxyphenol 20. Also, 3,4-dimethoxyacetophenone 21 was found, indicating the presence of 3-methoxy-4-hydroxyacetophenone 19 in the oxidation reaction mixture. 

Acetophenone, methyl-/7-tolyl ketone p-chloroacetophenone, /7-bromoaceto-phenone, methyl -anisyl ketone, 2,4-di-methoxyacetophenone,2-methyl-4-metho-xyacetophenone, 5-methyl-2-methoxyace-tophenone, acetocumene, 2,5-trimethyl-acetophenone, 0-, m-, p-hydroxyaceto-phenone, 2,4-dihydroxyacetophenone, 3-methoxy-4-hydroxyacetophenone, o-nitroacetophenone, m-nitroacetopheno-ne, /7-nitroacetophenone, o-, m-, /7-ami-noacetophenone, 2-aceto-l -naphthoxy-acetic acid, 2-aceto-4-bromo-l-naphtho-xyacetic acid... 

For further confirmation of the structure 4-1, the total synthesis was accomplished. When 2-methoxy-4-hydroxybenzaldehyde refluxed with bromoisoprene in acetone with presence of anhydride potassium carbonate an ether 4-5 was obtained. Compound 4-5 was put on Claisen rearrangement in butyric anhydride and N-dimethylaninine under nitrogen to yield butyrate 4-6, then hydrolyzed to 4-3. Finally, condensation of 4-3 with p-hydroxyacetophenone was carried out in the presence of HC1 to produce licochalcone (Scheme 7). This was identified with authentic... 

Precocene II (125) and other chromenes have been synthesized and screened for their effect on the cloth moth. Precocene II has larvicidal properties. A trifluoro-compound (126), related to precocene, has been synthesized from 3,4-dimethoxyphenol, trifluoroacetone, and allylmagnesium bromide. Several natural chromenes, for example 6-acetyl-2,2-dimethyl-5-hydroxy-8-methoxy-2//-chromene, have been synthesized from the appropriate substituted 2-hydroxyacetophenone and either 2-methylbut-3-en-2-ol or 3-chloro-3-methylbut-l-yne. 2//-Chromenes are rarely prepared from chromanones, but a direct conversion of substituted 2,2-dimethylchromanones, e.g. (127), in high yield, into 2H-chromenes, e.g. (128), has been achieved by the action of PCls. °... 

Acetophenone, 4 -hydroxy- Acetophenone, p-hydroxy-. See p-Hydroxyacetophenone Acetophenone, 4 -isopropyl-. See p-Isopropylacetophenone Acetophenone, 2-methoxy-2-phenyl-. See Benzoin methyl ether... 

Ethanone, 1-(2-hydroxy-5-nonylphenyl)-, oxime. See 2-Hydroxy-5-nonylacetophenone oxime Ethanone, 1-(2-hydroxyphenyl)-. Seeo-Hydroxyacetophenone Ethanone, 1-(3-hydroxyphenyl)-. Seem-Hydroxyacetophenone Ethanone, 1-(4-hydroxyphenyl)-. Seep-Hydroxyacetophenone Ethanone, 2-methoxy-1,2-diphenyl-. See Benzoin methyl ether Ethanone, 1-(4-methoxyphenyl)-. See Acetanisole... 

Preparation by reaction of chlorine on 4-chloro-3,6-di-methoxy-2-hydroxyacetophenone in chloroform at r.t. (57%) [1884],... 

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