Direct Acylation of Phenol and Naphthol Derivatives in a Mixture of Graphite and Methanesulfonic Acid

Abstract

Graphite in methanesulfonic acid is used to prepare o-hydroxyketones by direct acylation of phenol and naphthol derivatives with carboxylic acids.

Some Novel [6-(Isoxazol-5-ylmethoxy)-3-methylbenzofuran-2-yl]phenylmethanone Derivatives, Their Antimicrobial Activity, and Molecular Docking Studies on COVID-19

“…1-[2-Hydroxy-4-(prop-2-yn-1-yloxy)phenyl]ethanone (3) was subjected to condensation -cyclisation process with phenacyl bromide (5) in the presence of potassium carbonate with formation of [3-methyl-6-(prop-2-yn-1-yloxy)benzofuran-2-yl]-(phenyl)methanone (6) [12]. Some aliphatic and aromatic oxime intermediates 7a-7p were synthesized according to the presented earlier methods [13]. Alkyl oximes were synthesized by heating their precursors, alkyl aldehyde, with hydroxyl amine hydrochloride in presence of sodium acetate in MeOH at room temperature.…”

“…Attachment of other heterocyclic rings to benzofuran may lead to compounds of even higher activity against bacteria resistant to other drugs [7]. A number of natural and synthetic isoxazole based analogues such as ibotenic acid [8][9][10], muscimol [11] and some more exhibited valuable biological activities. Motivated by the above information on benzofuran and isoxazole derivatives, we have synthesized conjugated benzofuran-isoxazole derivatives targeting the potential pharmacophores.…”

Comparisons of O-acylation and Friedel–Crafts acylation of phenols and acyl chlorides and Fries rearrangement of phenyl esters in trifluoromethanesulfonic acid: effective synthesis of optically active homotyrosines

“…18 However, a previous study reported that mainly o-acylated isomer was afforded by the treatment of m-cresol and carboxylic acid with graphite and methanesulfonic acid at 120 °C in several hours. 19 On the other hand, our conditions, which were carried out at room temperature, afforded 4-and 6-acetylated isomers with a 1.4~2 : 1 ratio . The reaction condition can be applied to various carbon chains of macyloxy toluenes in good yield (Table 3, entry 4). 4-Fluoro-, 4-chloro-and 4-bromo-phenylacetate or phenylbenzoate have to heated at 60°C in neat TfOH to achieve Fries rearrangements in good yield (Table 3 entries 5-7).…”

Iron‐Doped Single‐Walled Carbon Nanotubes as New Heterogeneous and Highly Efficient Catalyst for Acylation of Alcohols, Phenols, Carboxylic Acids and Amines under Solvent‐Free Conditions

“…The following compounds obtained in this paper are known compounds: 2‐bromophenyl acetate8k ( 1 ), 2‐methoxyphenyl acetate18 ( 2 ), 2‐nitrophenyl acetate19 ( 3 ), 2,4‐dimethylphenyl acetate20 ( 4 ), 3‐tolyl acetate21 ( 5 ), 3,5‐dimethylphenyl acetate22 ( 6 ), 3‐fluorophenyl acetate23 ( 7 ), 4‐benzylphenyl acetate24 ( 8 ), 4‐bromophenyl acetate25a ( 9 ), 4‐chlorophenyl acetate25b ( 10 ), 4‐ tert ‐butylphenyl acetate8i ( 11 ), 4‐nitrophenyl acetate26 ( 12 ), naphthalen‐1‐yl acetate6e ( 13 ), naphthalen‐2‐yl acetate27 ( 14 ), phenyl acetate6e ( 15 ), 8‐hydroxy‐9,10‐dioxo‐9,10‐dihydroanthracen‐1‐yl acetate28 ( 16 ), 4‐methoxyphenyl acetate29 ( 17 ), (4‐chlorophenyl)(diethoxyphosphoryl)methyl acetate30a ( 18 ), (diethoxyphosphoryl)( p ‐tolyl)methyl acetate30a ( 19 ), (diethoxyphosphoryl)( m ‐tolyl)methyl acetate30a ( 20 ), (diethoxyphosphoryl)(phenyl)methyl acetate30a ( 21 ), acetic acid 10,13‐dimethyl‐17‐octyl‐2,3,4,7,8,9,10,11,12,13,14,15,16,17‐tetradecahydro‐1 H ‐cyclopenta[ a ]phenanthren‐3‐yl ester31 ( 22 ), acetic acid 2‐oxo‐1,2‐diphenylethyl ester30b ( 23 ), (1 R ,2 R ,5 R )‐2‐isopropyl‐5‐methylcyclohexyl acetate32 ( 24 ), 1‐phenylethyl acetate33 ( 25 ), benzyl acetate32 ( 26 ), 2‐nitrobenzyl acetate34 ( 27 ), acetic acid dodecyl ester35 ( 28 ), 2‐methyl‐1‐phenylpropan‐2‐yl acetate32 ( 29 ), 4‐methoxyphenyl benzoate36 ( 30 ), 4‐chlorophenyl benzoate36 ( 31 ), dodecyl benzoate37 ( 32 ), 4‐methoxyphenyl 2‐chlorobenzoate38 ( 33 ), 4‐methoxyphenyl 2‐phenylacetate39 ( 34 ), 4‐methoxyphenyl 4‐methylbenzoate40 ( 35 ), phenyl 2‐chloroacetate41 ( 36 ), 4‐methoxyphenyl thiophene‐2‐carboxylate42 ( 37 ), 3,6,9,12‐tetraoxa‐18‐azabicyclo[12.3.1]octadeca‐1(18),14,16‐triene‐2,13‐dione43 ( 38 ), N ‐phenylacetamide26 ( 39 ), N ‐(2‐cyanophenyl)acetamide44 ( 40 ), N ‐(4‐bromophenyl)acetamide43 ( 41 ), N ‐(4‐nitrophenyl)acetamide26 ( 42 ), N ‐(4‐cyanophenyl)acetamide45 ( 43 ), N ‐(2‐chlorophenyl)acetamide46 ( 44 ), N ‐(3‐hydroxyphenyl)acetamide47a ( 45 ), N ‐(4‐acetylphenyl)acetamide47b ( 46 ), 2‐acetamidobenzoic acid48 ( 47 ), 5‐acetamido‐2‐hydroxybenzoic acid49 ( 48 ), N ‐(3‐bromophenyl)acetamide50 ( 49 ), N‐o ‐tolylacetamide…”