50690-12-5

Usage

Synthesis Reference(s)

Synthesis, p. 895, 1974 DOI: 10.1055/s-1974-23475

InChI:InChI=1/C11H13ClO/c1-7-4-8(2)11(9(3)5-7)10(13)6-12/h4-5H,6H2,1-3H3

Upstream product

• 1667-01-2 2,4,6-Trimethylacetophenone 
• 79-11-8 chloroacetic acid 
• 108-67-8 1,3,5-trimethyl-benzene 
• 79-04-9 chloroacetyl chloride 
• 182115-37-3 2-oxo-2H-chromen-7-yl chloroethanoate 
• 105738-24-7 7-chloroacetyloxy-4-methylcoumarin 

Downstream Products

• 65782-65-2 2-benzothiazol-2-ylsulfanyl-1-(2,4,6-trimethyl-phenyl)-ethanone 
• 6682-69-5 5,7-dimethylindan-1-one 
• 1667-01-2 2,4,6-Trimethylacetophenone 
• 41841-19-4 methyl 2-mesitylacetate 
• 99376-43-9 1-(3-Chloro-2,4,6-trimethyl-phenyl)-ethanone 
• 99797-27-0 2,4,6-trimethylthiocyanatoacetophenone 
• 80707-10-4 2-chloro-1-(2,4,6-trimethylphenyl)ethanol 
• 67159-32-4 N-(2-mesityl-2-oxoethyl)formamide 
• 4408-60-0 2-mesitylacetic acid 
• 78830-31-6 (E)-1,2-dimesitoylethene 
• 859970-12-0 benzofuran-2-yl-mesityl ketone 
• 99797-34-9 2-imino-5-(2,4,6-trimethylphenyl)-1,3-oxathiole hydrochloride 
• 50447-68-2 2-(2,4,6-trimethylphenyl)oxirane 
• 480-63-7 mesitylenecarboxylic acid 

Relevant academic research and scientific papers

Synthetic process of 2,4,6-trimethyl benzoic acid

The invention discloses a synthetic process of 2,4,6-trimethyl benzoic acid; 2,4,6-trimethyl benzoic acid can be used as an intermediate for dyes, insecticides, medicines and photoinitiators, and can be used for synthesizing trimethyl benzoyl chloride, a hardening agent for polyepoxide and a photoinitiator for a polymer. The synthetic process successively includes an acylation reaction, a chloroform reaction and a hydrolysis reaction and includes the following steps: (1), acylation reaction: taking sym-trimethylbenzene and chloroacethyl chloride as acylation raw materials, adopting an acylation catalyst, heating, filtering and acidifying the filtrate to prepare 2,4,6-trimethyl chloroacetophenone; (2), chloroform reaction: with the product obtained in the step (1) and sodium hypochlorite as raw materials, adopting a quaternary ammonium salt as a phase transfer catalyst, heating, carrying out a reduction reaction to prepare 2,4,6-trimethyl benzoic acid; and (3), hydrolysis reaction: carrying out extraction liquid dividing, acid neutralization and re-crystallization of the product obtained in the step (2).

Chloroacetylation of arenes using chloroacetyl chloride in the presence of FeCl3 modified montmorillonite K10

Chloroacetylation reaction of arenes using chloroacetyl chloride has been studied in the presence of Fe-modified montmorillonite K10 catalysts in a liquid phase. The catalysts have been prepared by treating montmorillonite K10 with aqueous solution of FeCl3. Good yields and selectivity are observed for the acylated product.

Friedel-Crafts acylation of aromatic compounds with carboxylic acids in the presence of P2O5/SiO2 under heterogeneous conditions

A convenient and efficient procedure for the Friedel-Crafts acylation of aromatic compounds with carboxylic acids in the presence of P2O5/SiO2 is described. Both aromatic and aliphatic carboxylic acids reacted easily to afford the corresponding aromatic ketones. The use of non-toxic and inexpensive materials, simple and clean work-up, short reaction times and good yields of the products are the advantages of this method.

An efficient bismuth(III) chloride-catalyzed synthesis of 1,1-di-arylalkenes via Friedel-Crafts reaction of acyl chloride or vinyl chloride with arenes

In the presence of catalytic amount of bismuth(III) chloride, the reactions of acyl chlorides or vinyl chlorides with arenes afforded 1,1-diarylalkenes in 25-82% isolated yield. In the case of the reaction of acyl chlorides with arenes, the procedure includes an initial Friedel-Crafts acylation, subsequent formation of vinyl chlorides and final Friedel-Crafts-type vinylation of another arene molecule with vinyl chloride. This paper reports the first Lewis acid-catalyzed cleavage of the C-Cl bond of vinyl chloride and its application in the synthesis of multiply subtituted alkenes.

Intermolecular character of the Fris rearrangement in the series of acyloxycoumarins

In the study of the Fris rearrangement in the series of 7-and 4-acyloxycoumarins we obtained certain data indicating intermolecular character of the rearrangement. The Fris rearrangement of a mixture of 7-benzoyloxy-4-metylcoumarin and 7-acetoxycoumarin results in formation of four reaction products in approximately equal molar ratio. Also, four products were obtained in the Fris rearrangement of 7-and 4-acyloxycoumarins in the presence of hydroxycoumarins. The Fris rearrangement of acyloxycoumarins in the presence of m-xylene at acylcoumarin-m-xylene ratio of 1:6 leads to the corresponding hydroxycoumarins and acylated m-xylenes. Intermediate formation of acylium ions was also detected by evolution of carbon monooxide at the Fris rearrangement of 7-pyvaloyloxy-and 7-isobutyryloxy-4-methylcoumarins. A product of intermolecular migration, 3-acetyl-4-hydoxy-6-methylcoumarin, was discovered also in the rearrangement of 4-acetoxycoumarin in the presence of 4-hydoxy-6-methylcoumarin catalyzed by phosphorus oxychloride.

Photoenolization with α-Chloro Substituents

Irradiation of a methanol solution of 2,5-dimethyl-α-chloropropiophenone (1a) produces 2,6-dimethyl-1-indanone (2a), 2-(methoxymethyl)-5-methylpropiophenone (3a), 2,5-dimethylpropiophenone (4a), and methyl 2-(2,5-dimethylphenyl)propionate (5a).It is proposed that the first two products arise from hydrogen abstraction followed by chlorine loss, the latter two from initial loss of chlorine.Making the chlorine-bearing carbon primary suppresses the formation of the latter two products, while maintaining the carbonyl nearly planar with the ring suppresses all product formation.Other examples are presented.