43108-74-3

Basic information

• Product Name: 1-Butanone, 3-hydroxy-3-Methyl-1-phenyl-
• Synonyms: 1-Butanone, 3-hydroxy-3-Methyl-1-phenyl-
• CAS NO: 43108-74-3
• Molecular Formula: C₁₁H₁₄O₂
• Molecular Weight: 178.22766
• Mol File: 43108-74-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Butanone, 3-hydroxy-3-Methyl-1-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Butanone, 3-hydroxy-3-Methyl-1-phenyl-(43108-74-3)
• EPA Substance Registry System: 1-Butanone, 3-hydroxy-3-Methyl-1-phenyl-(43108-74-3)

Safety Data

• Hazardous Substances Data: 43108-74-3(Hazardous Substances Data)

Usage

Synthesis

To a four-necked flflask, equipped with a mechanical stirrer, a reflflux condenser with a nitrogen inlet, a thermometer, and a pressure-equalizing dropping funnel, was added 36 g (0.30 mol) of acetone and 41.4 g (0.41 mol) of triethylamine under a nitrogen atmosphere. To this mixture, stirred at room temperature under nitrogen, was added via the dropping funnel 43.2 g (0.40 mol) of chlorotrimethylsilane over 10 min. ?The flflask was then immersed in a water bath and the contents were warmed to 35°C.?The water bath was removed and the dropping funnel was charged with a solution of 60 g (0.40 mol) of sodium iodide in 350 mL of acetonitrile. This solution was added to the stirred mixture in the flflask at such a rate that the temperature of the reaction was maintained at 34–40 °C without external heating or cooling. The addition required approximately 1 h. When the addition was complete, the reaction mixture was stirred for a further 2 h at room temperature. The contents of the flflask were then poured into ice-cold water, and the aqueous mixture was extracted three times with pentane. After extraction, the organic layer was dried over potassium carbonate and then concentrated with a rotary evaporator under reduced pressure. The crude product was a mixture of 97% of the desired silyl enol ether and 3% of acetophenone, as shown by gas chromatography. The crude product was distilled in a Claisen flflask at a pressure of about 40 mm. After a small forerun (about 3 g), 52.3 g (91%) of silyl enol ether, bp 124–125.5°C, was obtained. The purity of this material was approximately 98%, as judged by gas chromatography and 1 H NMR spectroscopy.

Upstream product

• 98-86-2 acetophenone 
• 67-64-1 acetone 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 144741-40-2 3-methyl-1-phenyl-3-(trimethylsilyloxy)butan-1-one 
• 70-11-1 α-bromoacetophenone 
• 78175-62-9 3-Hydroxy-2-isopropyl-N,N-dimethyl-3-phenyl-thiobutyramide 
• 15120-98-6 (3,3-dimethyl-oxiranyl)-phenyl-methanone 
• 583-05-1 1-phenylpentane-1,4-dione 
• 2206-94-2 1-acetoxy-1-phenylethene 
• 67-63-0 isopropyl alcohol 
• 39623-95-5 1-phenylprop-1-enyl acetate 
• 7653-94-3 1,1-dimethyl-2-phenylcyclopropane 
• 104174-42-7 (±)-1-methyl-4-phenylbutane-2,4-diol 
• 34586-02-2 1,2-Dimethyl-3-phenylpropylhydroperoxid 

Downstream Products

• 5650-07-7 3-methyl-1-phenyl-but-2-en-1-one 
• 98-86-2 acetophenone 
• 67-64-1 acetone 
• 84599-53-1 2-methyl-4-phenyloctane-2,4-diol 
• 21133-79-9 2-methyl-4-phenyl-pentane-2,4-diol 
• 109398-10-9 1,1-diphenyl-3-methylbutane-1,3-diol 
• 175849-02-2 Trifluoro-acetic acid 1,1-dimethyl-3-oxo-3-phenyl-propyl ester 
• 103668-44-6 (1SR,1RS)-1-phenyl-4-methylpentane-1,3-diol 
• 134924-34-8 3,3-Dimethyl-5-oxo-5-phenyl-pentanoic acid ethyl ester 
• 133817-09-1 2,3,3-Trimethyl-5-oxo-5-phenyl-pentanoic acid ethyl ester 
• 103-05-9 4-phenyl-2-methyl-2-butanol 
• 89881-71-0 fluoro(dimethyl)(2-methyl-4-phenylbutan-2-yl)silane 
• 89881-67-4 3-dimethyl(phenyl)silyl-3-methyl-1-phenylbutane 
• 167282-21-5 3-dimethyl(phenyl)silyl-3-methyl-1-phenylbutan-1-one 

Relevant articles and documents

All at once arrangement of both oxygen atoms of dioxygen into aliphatic C(sp3)-C(sp3) bonds for hydroxyketone difunctionalization

Both β- and γ- hydroxyketone structures are important units in biologically active molecules, synthetic drugs and fine chemicals. Although there are some routes available for their manufacture from pre-functionalized groups on one or two matrix molecule(s), the approaches to simply and simultaneously deposit two oxygen atoms from dioxygen into two specific C(sp3) positions of pure saturated hydrocarbons have rarely succeeded because they are involved in the targeted activation of three inert C-H σ bonds all at once. Here, we show that a TiO2-CH3CN photocatalytic suspension system enables the insertion of dioxygen into one C(sp3)-C(sp3) bond of strained cycloparaffin derivatives, by which difunctionalized hydroxyketone products are obtained in a one-pot reaction. With the cleavage event to release strain as the directional driving force, as-designed photocatalytic reaction systems show 21 examples of β-hydroxyketone products with 31%–76% isolated yields for three-membered ring derivatives and 5 examples of γ-hydroxyketone products with 30%–63% isolated yields for four-membered ring substrates. 18O isotopic labeling experiments using 18O2, Ti18O2 and intentionally added H218O, respectively, indicated that both oxygen atoms of hydroxyketone products were exclusively from dioxygen, suggesting a previously unknown H+/TiO2-e? catalyzed arrangement pathway of the hydroperoxide intermediate to convert dioxygen into hydroxyketone units. [Figure not available: see fulltext.]

Pd-catalyzed imine-directed intramolecular C–N bond formation through C(sp3)–H activation: An efficient approach to multisubstituted pyrroles

An atom-economic approach to synthesize 1,2,4-trisubstituted pyrroles through palladium-catalyzed imine-directed intramolecular C(sp3)–H amination reaction has been developed. The imine group acts as a directing group as well as an intramolecular nucleophile for the first time in intramolecular C–N bonds formation reactions.

Β - hydroxy ketone compounds

The invention provides a synthesis method for a beta-hydroxy-ketone compound shown in a formula (III). The method comprises the steps that substitute vinyl acetate shown in a formula (I), a substitute alcohol compound shown in a formula (II) and an oxidizing agent are mixed to obtain reaction liquid, and the reaction liquid reacts for 2-12 hours at the temperature of 20 DEG C-120 DEG C, and then is treated to obtain the beta-hydroxy-ketone compound. The method is safe and environmentally friendly, and is a new path for synthesizing the beta-hydroxy-ketone compound containing various substituents, the substrate adaptability is good, and the reaction operation is easy.

Metal-Free tert -Butyl Hydrogenperoxide (TBHP) Mediated Radical Alkylation of Enol Acetates with Alcohols: A New Route to β-Hydroxy Ketones

A metal-free TBHP-mediated radical alkylation of enol acetates with alcohols is described. This method provides a new route to a variety of β-hydroxy-ketones in moderate to good yields.

The Stereochemical Course of the α-Hydroxyphosphonate-Phosphate Rearrangement

The phosphonate-phosphate rearrangement is an isomerisation of α-hydroxyphosphonates bearing electron-withdrawing substituents at the α-carbon atom. We studied the stereochemical course of this rearrangement with respect to phosphorus. A set of four diastereomeric α-hydroxyphosphonates was prepared by a Pudovik reaction from two diastereomeric cyclic phosphites. The hydroxyphosphonates were separated and rearranged with Et3N as base. In analogy to trichlorphon, which was the first reported compound undergoing this rearrangement. All four hydroxyphosphonates could be rearranged to 2,2-dichlorovinyl phosphates. Single-crystal X-ray structure analyses of the α-hydroxyphosphonates and the corresponding phosphates allowed us to show that the rearrangement proceeds with retention of configuration on the phosphorus atom.

Trichlorosilyl triflate-mediated enantioselective directed cross-aldol reaction between ketones using a chiral phosphine oxide as an organocatalyst

Trichlorosilyl triflate-promoted directed cross-aldol reaction between ketones in the presence of a chiral phosphine oxide as an organocatalyst is described. This is the first enantioselective cross-aldol reaction between simple ketones with good enantioselectivity.

METHODS OF MAKING DIASTEREOMERIC ORGANIC COMPOUNDS

Disclosed is a process for making diastereomeric compound of the formula (I): wherein m, n and R1 to R4 are as defined herein. The process of the invention provides the compound of formula (I) in high yield and substantially free of

The zirconium alkoxide-catalyzed aldol-tishchenko reaction of ketone aldols

The aldol-Tishchenko reaction of ketone aldols as enol equivalents has been developed as an efficient strategy to furnish differentiated 1,3-anti-diol monoesters in one step. The thermodynamically unstable ketone aldols undergo a facile retro-aldolization to yield a presumed zirconium enolate in situ, which then undergoes the aldol-Tishchenko reaction in typically high yields and with complete 1,3-anti diastereocontrol. Evaluation of a broad range of metal alkoxides as catalysts and optimization of the reaction protocol led to a modified zirconium alkoxide catalyst with attenuated Lewis acidity and dichloromethane as solvent, which resulted in suppression of the undesired acyl migration to a large extent. Various ketone aldols have been prepared and subjected to the general process, giving rise to a broad range of differently substituted 1,3-anti-diol monoesters, which may be hydrolyzed to the corresponding 1,3-anti-diols.

Mukaiyama Aldol Reactions of Silyl Enolates Catalyzed by Iodine

Iodine catalyzed Mukaiyama aldol reaction of silyl enol ethers and silyl ketene acetal with aldehydes, ketones and acetals in good yield with preferential antiselectivity has been described.

The indium(III) chloride-catalysed hydrolysis and in situ Mukaiyama-type reaction of arylmethyl ketone derived silyl enol ethers under solvent-free conditions

Treatment of trimethylsilyl enol ethers of arylmethyl ketones with catalytic amounts of indium(III) chloride under solvent-free conditions leads to a remarkably efficient process of in situ hydrolysis and Mukaiyama-type addition to the resulting ketones.