4-Methoxyphenyl acetate hydrolysis

Phenols can also be prepared by combining two reactions that you have seen previously Baeyer-Villiger oxidation and ester hydrolysis. Oxidation of p-methoxyacetophenone with trifluoroperoxyacetic acid gives 4-methoxyphenyl acetate as the major product and methyl 4-methoxybenzoate as the minor one. 

Hydrolysis of the ester group of 4-methoxyphenyl acetate gives 4-methoxyphenol. 

Preparation by hydrolysis of 4-acetyl-3-methoxyphenyl acetate with boiling 10% sodium hydroxide solution (58%) [2791] or 4-acetyl-3-methoxyphenyl benzoate with potassium hydroxide in refluxing methanol (85%) [2792]. 

Also obtained by hydrolysis of 4-acetyl-2-methoxyphenyl acetate with boiling water [2784],... 

Also obtained by hydrolysis of ethyl 2,4-dimethoxybenzoyl-4-methoxyphenyl-acetate (m.p. 48-50°) in acetic acid with concentrated hydrochloric acid on a steam bath for 15 h (33%) [5211]. 

N-Acylation of 2-methyl-5,6-dihydro-4/f-l,3-thiazine with cinnamoyl chloride in the presence of triethylamine furnishes ( )-l-(2-methylenetetrahydro-l,3-thiazin-3-yl)-3-arylprop-2-en-l-ones 122. These products undergo hydrolysis readily due to the j jA -ketene acetal-type bonds present in the molecules and are therefore not stable. Thus ( )-3-(3-(4-methoxyphenyl)acrylamido)propyl ethanethioate 123 is isolated in 92% yield from the corresponding thiazine after column chromatography on Si02 or AI2O3 <2001S135>. 

Diastereoselective [2+2] photocycloaddition of a polymer-supported cyclic chiral enone with ethylene has been reported (Scheme 12.33) [43]. The auxiliary was derived from (-)-8-(p-methoxyphenyl) menthol (87). Protection of the secondary alcohol and demethylation were carried out to give (-)-8-(p-hydroxyphenyl)menthyl acetate (88). An alkyl linker was introduced and finally loaded to poly (ethylene glycol) grafted Wang resin. Deprotection of the alcohol functionality was followed by esterification with cyclohexen-3-one-l-carboxylic acid to provide the chiral enone 89. The photochemical reaction with ethylene was performed by irradiating with light (k > 280 nm). Trifluoroacetic acid (TFA) or aqueous hydrolysis with... 

El-Amamy and Mill (1984) measured the effect of the surface acidity of mont-morillonite and kaolinite on the hydrolysis rate constants for a number of chemicals containing hydrolyzable functional groups that exhibit acid-catalyzed, base-catalyzed, and neutral hydrolysis. The chemicals that were studied included ethyl acetate, cyclohexene oxide, isopropyl bromide, l-(4-methoxyphenyl)-2,3-epoxypropane, and N-methyl-p-tolyl carbamate (MTC). Aqueous suspensions of... 

When 14 was heated in ethanol under reflux with hydrochloric acid, (Z)-[4-(5-hydroxy-3-methyl-l-phenyl-lH-pyrazol-4-ylmethyhdene)-5-oxo-l-phenyl-4,5-dihydro-lH-pyrazol-3-yl] acetate (17) was obtained in 75% yield, identical with the compound prepared from 14 and 12 in 90% yield. Apparently, partial hydrolysis of enamine 14 took place to furnish in situ pyrazole 12, which reacted as the C-nucleophile with the non-hydrolysed enaminone 14 to afford 17. Compounds 15 were heated with 2 equivalents of DMFDMA in DMF under reflux to give pyrazolo[4,3-c] pyridines 18 in moderate yields. Cyclization proceeds by incorporation of DMFDMA as a Ci synthon between the nucleophilic NH and CH2 groups. In the reaction of 15 (R =4-hydroxyphenyl) with DMFDMA, methylation of the phenolic hydroxy group also took place to give the 5-(4-methoxyphenyl)pyrazolo[4,3-c]pyridine (18 R=4-methoxyphenyl) (Scheme 7). 

The imidazole-catalysed hydrolysis of polar substituted 2,4-dinitrophenyl acetates (21 X = Cl, OMe) has been investigated at different temperatures. The observed rates correspond to the bimolecular nucleophilic addition of the imidazole at the carboxylic carbon atom followed by a very fast hydrolysis of the (V-acetylimidazole in water. The influence of polar substituents in the acid moiety of the ester molecule on the hydrolysis reaction can be described by an electrostatic dipole-dipole interaction in the same way as the neutral hydrolysis of polar substituted ethyl acetates. By the use of both quantum and classical dynamics, a study of the neutral hydrolysis of 4-methoxyphenyl dichloroacetate (22) in water concluded that the rate-determining step is a proton transfer concerted with formation of a C-O bond. ... 

Obtained by hydrolysis of l-(2,4-diacetoxy-3,5,6-tri-methoxyphenyl)ethanone (SM) with aqueous 10% sodium hydroxide at r.t. for 10-15 min. SM was obtained by Friedel-Crafts acylation of 2,3,5,6-tetramethoxyphenylacetate(m.p. 97-98°) with acetic anhydride/acetic acid in the presence of excess boron trifluoride at 50-60° for 5 h (65%, m.p. 82-84°) [3316]. 

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