16475-85-7

Basic information

• Product Name: 2'-Hydroxy-4'-methyl-5'-acetylacetophenone
• Synonyms: 2,4-Diacetyl-5-methylphenol;2'-Hydroxy-4'-methyl-5'-acetylacetophenone
• CAS NO: 16475-85-7
• Molecular Formula: C₁₁H₁₂O₃
• Molecular Weight: 192.21
• Mol File: 16475-85-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 108°C
• Appearance: /
• CAS DataBase Reference: 2'-Hydroxy-4'-methyl-5'-acetylacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-Hydroxy-4'-methyl-5'-acetylacetophenone(16475-85-7)
• EPA Substance Registry System: 2'-Hydroxy-4'-methyl-5'-acetylacetophenone(16475-85-7)

Safety Data

• Hazardous Substances Data: 16475-85-7(Hazardous Substances Data)

Usage

Preparation

Preparation by cyclization of 1,1,3,3-tetraacetylpropene (formerly so called methenylbisacetylacetone) (SM) (m.p. 117–118°) , ? by adding a solution of SM (1 mol) in benzene to a sodium methoxide (4 mol) or magnesium methoxide (4 mol) solution in methanol and set aside for 24 h (quantitative yields) ; ? on heating of its potassium salt in alcoholic solution for 6–8 h at reflux. SM was prepared by treatment of ethoxymethyleneacetylacetone (m.p. 140–142°) with the potassium salt of acetylacetone in ethanol.

Upstream product

• 4110-55-8 3,5-diacetylheptane-2,6-dione 
• 31517-59-6 4,6-diacetyl-3-methyl-cyclohex-2-enone 
• 33884-41-2 ethoxylideneacetylacetone 
• 15435-71-9 sodium acetylacetonate 
• 71043-43-1 1,1'-(2-hydroxy-2,6-dimethyl-2H-pyran-3,5-diyl)-bis-ethanone 
• 30561-07-0 5-nitro-2,4-dimethoxypyrimidine 
• 123-54-6 acetylacetone 
• 122-46-3 3-acetoxytoluene 
• 54283-20-4 1,1,2,2-Tetraacetylcyclopropane 
• 68541-87-7 1-(2-methyl-5-nitropyridin-3-yl)ethanone 
• 90860-45-0 4-methoxy-6-methyl-5-nitropyrimidine 
• 14080-32-1 5-nitropyrimidine 
• 15579-58-5 5-nitro-4-methoxypyrimidine 
• 67-66-3 chloroform 

Downstream Products

• 131941-98-5 (E)-1-{2-Hydroxy-5-[(E)-3-(4-methoxy-phenyl)-acryloyl]-4-methyl-phenyl}-3-(4-methoxy-phenyl)-propenone 
• 108-39-4 3-methyl-phenol 
• 131941-99-6 2-(4-Methoxy-phenyl)-6-[(E)-3-(4-methoxy-phenyl)-acryloyl]-7-methyl-chromen-4-one 
• 131942-01-3 (E)-1-{4-Hydroxy-5-[5-(4-methoxy-phenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl]-2-methyl-phenyl}-3-(4-methoxy-phenyl)-propenone 

Relevant articles and documents

Copper-catalyzed synthesis of phenolic compounds with DMSO as the methylene source

The application of DMSO as an ideal source of carbon is highly attractive. A simple and novel protocol has been developed for the synthesis of phenolic compounds via CuSO4·5H2O-catalyzed cyclization of 1,3-dicarbonyl compounds with DMSO. It was found that the unsymmetrical 1,3-dicarbonyl compounds always gave a mixture of two isomeric products. In addition, the deuterium-labeling experiments revealed that the C2 in benzene rings resulted from DMSO.

Palladium-catalyzed formation of phenolic compounds by reaction of carbonyl compounds with carbon dioxide

The use of carbon dioxide as a renewable and environmentally friendly source of carbon is highly attractive. A novel and efficient protocol for the synthesis of phenolic compounds from carbonyl compounds and carbon dioxide in the presence of a catalytic amount of Pd(OAc)2 has been developed. This reaction is appealing for industries and is a tool for the sequestration of carbon dioxide.

Synthesis of some new heterocyclic derivatives: Part 1. Cinnamoylflavones and a related pyrazoline derivative

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