64794-45-2

Basic information

• Product Name: Ethanone, 1-(2,5-dihydroxy-3,4,6-trimethylphenyl)-
• Synonyms: 2,3,5-trimethyl-3,6-dihydroxyacetophenone;2,5-dihydroxy-3,4,6-trimethylacetophenone;acetyl-trimethylhydroquinone;2,5,6-trimethyl-3-acetyl-hydroquinone;3,4,6-trimethyl-2,5-dihydroxyacetophenone
• CAS NO: 64794-45-2
• Molecular Formula: C11H14O3
• Molecular Weight: 194.23
• Mol File: 64794-45-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Ethanone, 1-(2,5-dihydroxy-3,4,6-trimethylphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-(2,5-dihydroxy-3,4,6-trimethylphenyl)-(64794-45-2)
• EPA Substance Registry System: Ethanone, 1-(2,5-dihydroxy-3,4,6-trimethylphenyl)-(64794-45-2)

Safety Data

• Hazardous Substances Data: 64794-45-2(Hazardous Substances Data)

Upstream product

• 7446-70-0 aluminium trichloride 
• 7479-28-9 2,3,5-trimethyl-1,4-hydroquinone diacetate 

Downstream Products

• 133658-42-1 2,3-dihydro-2-phenyl-6-hydroxy-2,5,7,8-tetramethyl-4H-1-benzopyran-4-one 
• 34036-31-2 2-ethyl-3,5,6-trimethyl-hydroquinone 

Relevant articles and documents

Synthesis and oxidation behavior of 2,4,5,7,8-pentamethyl-4H-1,3-benzodioxin-6-ol, a multifunctional oxatocopherol-type antioxidant.

2,4,5,7,8-Pentamethyl-4H-1,3-benzodioxin-6-ol (PBD, 1) is a novel 3-oxa-tocopherol-type stabilizer, which is obtained as a mixture of two diastereomers by condensation of trimethylhydroquinone with acetaldehyde in an acid-catalyzed reaction. The oxidation behavior of 1 is governed by the amount of water available. In aqueous media, 1 is oxidized by one oxidation equivalent to 2,5-dihydroxy-3,4,6-trimethylacetophenone (3) via 2-(1-hydroxyethyl)-3,5,6-trimethylbenzo-1,4-quinone (2). The acid-catalyzed conversion of 2 into 3 proceeds in solution with first-order kinetics with regard to 2 but works also in solid phase. Oxidation in the presence of just 1 equiv of water produces acetophenone 3 as well, but according to a different mechanism involving o-quinone methide 5 and styrene derivative 6, from which finally acetaldehyde is released. A [1,5]-sigmatropic proton shift from the C-4a methyl group to the exocyclic methylene group in 5 causes formation of 6, as demonstrated by labeling experiments. In addition, the presence of both intermediates was proven by hetero-Diels-Alder trapping reactions. In the absence of water, oxidation of 1 produces chromenone 10 via the intermediates 5 and 6 and chromanone 9, and oxidation of 9 to 10 is preferred to oxidation of starting material 1. When the formation of an exocyclic methylene group at C-4 is impossible as a result of structural prerequisites, as in the diphenyl derivative 12, the initially generated o-quinone methide 5 cannot form 6 but undergoes dimerization to spiro-compounds. The transformation of p-quinone 2 into acetophenone 3 might contribute to the chemistry of tocopherols oxidized at C-4, i.e., 4-hydroxy-alpha-tocopherol and 4-oxo-alpha-tocopherol, which have been proposed as precursors of natural vitamin E metabolites.