14353-72-1

Basic information

• Product Name: 4-hydroxy-2,4,5-trimethyl-2,5-cyclohexadien-1-one
• Synonyms: 4-hydroxy-2,4,5-trimethyl-2,5-cyclohexadien-1-one
• CAS NO: 14353-72-1
• Molecular Weight: 152.193
• Mol File: 14353-72-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4-hydroxy-2,4,5-trimethyl-2,5-cyclohexadien-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-hydroxy-2,4,5-trimethyl-2,5-cyclohexadien-1-one(14353-72-1)
• EPA Substance Registry System: 4-hydroxy-2,4,5-trimethyl-2,5-cyclohexadien-1-one(14353-72-1)

Safety Data

• Hazardous Substances Data: 14353-72-1(Hazardous Substances Data)

Upstream product

• 95-63-6 1,2,4-Trimethylbenzene 
• 137-18-8 2,5-Dimethyl-1,4-benzoquinone 
• 917-54-4 methyllithium 
• 14353-67-4 N-(2,4,5-trimethyl-phenyl)-hydroxylamine 
• 496-78-6 2,4,5-trimethylphenol 
• 917-64-6 methyl magnesium iodide 

Downstream Products

• 114534-32-6 (4R,5R,6R)-4-Hydroxy-3,4,6-trimethyl-5-vinyl-cyclohex-2-enone 

Relevant articles and documents

Selective oxidation of pseudocumene and 2-methylnaphthalene with aqueous hydrogen peroxide catalyzed by γ-Keggin divanadium-substituted polyoxotungstate

The catalytic performance of a γ-Keggin divanadium-substituted phosphotungstate, (Bu4N)4[γ-PW10O38V2(μ-O)(μ-OH)], has been evaluated in the selective oxidation of 1,2,4-trimethylbenzene (pseudocumene, PC) and 2-methylnaphthalene with the green oxidant, 35% aqueous hydrogen peroxide. Under conditions of H2O2 deficiency ([PC]/[H2O2] = 17-22), PC oxidation proceeded with unusually high chemo- and regioselectivity, producing exclusively 2,4,5-trimethylphenol (2,4,5-TMP) and 2,3,5-TMP in a molar ratio of 7.3/1 and a yield of 73% based on the oxidant. Isomeric 2,3,6-trimethylphenol was found in trace amounts. Under conditions of H2O2 excess ([H2O2]/[PC] = 8), 2,3,5-trimethyl-1,4-benzoquinone (TMBQ, vitamin E key intermediate) formed with 41% selectivity at 41% substrate conversion. Atypical regioselectivity was also found in the oxidation of 2-methylnaphthalene which gave predominantly 6-methyl-1,4-naphthoquinone (6-MNQ) rather than isomeric 2-MNQ. The ratio between the isomers could be altered by varying the catalyst and oxidant amounts.

REACTIONS OF ORGANOLITHIUM REAGENTS WITH p-BENZOQUINONES AND CYCLOHEXADIENONS, SYNTHESIS OF 4-ALKYL-4-HYDROXYCYCLOHEXA-2,5-DIEN-1-ONES AND 1,4-DIALKYLCYCLOHEXA-2,5-DIENE-1,4-DIOLS.

Addition of organolithium reagents to p-benzoquinones in ether gives the corresponding 4-alkyl-4-hydroxycyclohexa-2,5-dien-1-ones.Addition of excess of the reagent to the p-benzoquinones, or to the 4-alkyl-4-hydroxycyclohexa-3,5-dien-1-ones, in tetrahydrofuran, gives the corresponding dialkylcyclohexa-2,5-diene-1,4-diols.