42117-30-6

Basic information

• Product Name: 2,5-Cyclohexadien-1-one, 2-methoxy-4,4-dimethyl-
• CAS NO: 42117-30-6
• Molecular Formula: C9H12O2
• Molecular Weight: 152.193
• Mol File: 42117-30-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2,5-Cyclohexadien-1-one, 2-methoxy-4,4-dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Cyclohexadien-1-one, 2-methoxy-4,4-dimethyl-(42117-30-6)
• EPA Substance Registry System: 2,5-Cyclohexadien-1-one, 2-methoxy-4,4-dimethyl-(42117-30-6)

Safety Data

• Hazardous Substances Data: 42117-30-6(Hazardous Substances Data)

Upstream product

• 4694-17-1 5,5-dimethlycyclohex-2-en-1-one 
• 74-88-4 methyl iodide 
• 1073-13-8 4,4-dimethylcyclohexenone 
• 84903-32-2 5,5-dimethyl-2-methylnitrono-3-cyclohexenone 
• 84903-28-6 5,5-dimethyl-2-nitro-1,3-cyclohexadienol 
• 84903-32-2 5,5-dimethyl-2-methylnitrono-3-cyclohexenone 
• 84903-31-1 2-hydroxyimino-5,5-dimethyl-3-cyclohexenone 
• 42117-29-3 2-hydroxy-4,4-dimethylcyclohexa-2,5-dien-1-one 
• 77-78-1 dimethyl sulfate 
• 42117-32-8 2-methoxy-4,4-dimethylcyclohex-2-en-1-one 

Downstream Products

• 146779-04-6 3-hydroxy-2-methoxy-6,6-dimethyl-1,4-cyclohexadiene 
• 85312-33-0 6,6-dimethoxy-5,5-dimethyl-2-cyclohexenone 
• 85312-32-9 2,2-dimethoxy-6,6-dimethylbicyclo<3.1.0>hexan-3-one 
• 1128-57-0 1,2-dimethoxy-4,5-dimethylbenzene 

Relevant articles and documents

The regioselectivity of the Birch reduction

The reaction mechanism of the Birch reduction was investigated with a view of determinig how the regioselectivity is controlled. Regioselectivity is determined in the first step of radical anion protonation and in the second step of cyclohexadienyl carbanion protonation. It was ascertained that the rate-determining step of the Birch reduction of anisole was radical anion protonation, consistent with the observation of Krapcho and Bothner-By in the case of benzene reduction. A new approach to determining the regioselectivity of the two steps of the Birch reduction was devised. This was predicated on an enhanced primary deuterium isotope effect anticipated for radical anion protonation relative to that expected for cyclohexadienyl carbanion protonation. The approach utilized a partially deuterated medium. The method was applied to the reductions of anisole, 1,3-dimethoxybenzene, 3-methoxytoluane, and 2-methoxynaphthalene. The basic assumption of greater selectivity of the radical anion of the first step relative to the carbanion of the second step was explored in the cases of benzene and anisole and confirmed. In the examples studied, ortho protonation of the radical anion was found to predominate. With a view of understanding the regioselectivity of the two steps, quantum mechanical computations were carried out on several facets of the reaction. Electron density distributions of the radical anions were determined as well as the energies of radical products of some radical anion protonations. Similarly, the energies were obtained for the partially protonated radical anion species at several points along the reaction coordinate. In addition, electron densities were obtained for cyclohexadienyl anion. Theory was then correlated with experiment.

Nitration of 2-Cyclohexenone Derivatives and Some Reactions of the Products

5,5-dimethyl-2-cyclohexenone (Ia) and isophorone (Ib) were nitrated with isoamyl nitrate using potassium metal in liquid ammonia to give 5,5-dimethyl-2-nitro-1,3-cyclohexadienol (III) and 3,5,5-trimethyl-2-nitro-2-cyclohexenone (IVb), respectively.Compoun

Chemistry of 2-Methoxy-2,5-cyclohexadienones. I. Photochemistry of 2-Methoxy-4,4-dimethyl-2,5-cyclohexadienone

The title compound, 2-methoxy-4,4-dimethyl-2,5-cyclohexadienone (V), was prepared from 2-methoxy-4,4-dimethyl-2-cyclohexenone (VIa).A methanolic solution of V was irradiated with a 200 W mercury lamp at -3 deg C to give 2,2-dimethoxy-6,6-dimethylbicyclo3