38857-84-0

Basic information

• Product Name: 2-methyl-1,3-diphenylpropan-1-ol
• Synonyms: 2-methyl-1,3-diphenylpropan-1-ol
• CAS NO: 38857-84-0
• Molecular Weight: 226.318
• Mol File: 38857-84-0.mol

Chemical Properties

• CAS DataBase Reference: 2-methyl-1,3-diphenylpropan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methyl-1,3-diphenylpropan-1-ol(38857-84-0)
• EPA Substance Registry System: 2-methyl-1,3-diphenylpropan-1-ol(38857-84-0)

Safety Data

• Hazardous Substances Data: 38857-84-0(Hazardous Substances Data)

Upstream product

• 93-54-9 1-Phenyl-1-propanol 
• 100-51-6 benzyl alcohol 
• 859056-89-6 1,3-diphenyl-2-methylprop-2-en-1-ol 
• 4842-43-7 2-methyl-1,3-diphenylpropan-1-one 
• 5445-77-2 2-benzylpropionaldehyde 
• 93-55-0 1-phenyl-propan-1-one 
• 65564-83-2 α-[(1E)-1-methyl-2-phenylethenyl]benzenemethanol 
• 591-51-5 phenyllithium 
• 123-62-6 propionic acid anhydride 
• 646516-78-1 5-Oxo-bicyclo[4.2.0]octane-1-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 342389-63-3 benzyl 2-benzoyl-2-methyl-3-phenylpropanoate 

Relevant articles and documents

Asymmetric hydrogenation of allylic alcohols using ir?N,P-Complexes

In this study, a series of γ,γ-disubstituted and β,γ-disubstituted allylic alcohols were prepared and successfully hydrogenated using suitable N,P-based Ir complexes. High yields and excellent enantioselectivities were obtained for most of the substrates studied. This investigation also revealed the effect of the acidity of the N,P?Ir-complexes on the acid-sensitive allylic alcohols. DFT ΔpKa calculations were used to explain the effect of the N,P-ligand on the acidity of the corresponding Ir-complex. The selectivity model of the reaction was used to accurately predict the absolute configuration of the hydrogenated alcohols.

Access to optically active linear ketones by one-pot catalytic deprotection, decarboxylation, asymmetric tautomerization from racemic benzyl β-ketoesters

Benzyl 2-benzoyl-2-phenylpropanoate 1b subjected to heterogeneous hydrogenolysis conditions in the presence of catalytic amounts of commercially available cinchonia alkaloids as chiral protic source, led to (R)-1,2-diphenylpropanone with up to 71% ee, through a cascade reaction involving deprotection, decarboxylation and asymmetric tautomerization of enolic species.

Ligand-free Guerbet-type reactions in air catalyzed by in situ formed complexes of base metal salt cobaltous chloride

Inexpensive, earth-abundant and environmentally benign cobaltous chloride efficiently accomplishes the catalytic β-alkylation of alcohols in air at 140 °C. At higher loadings of cobaltous chloride (1 mol%) in the presence of 2.5 mol% NaOtBu, there is a rapid formation of heterogeneous Co nanoparticles (NPs) which are apparently sensitive to air and result in poor yields (ca. 25%) of β-alkylated products. In contrast, performing the reaction in an argon atmosphere under otherwise identical conditions leads to higher yields (ca. 44%). The heterogenization and eventual loss of activity in air could be delayed by operating at a lower (0.01 mol%) CoCl2 loading in the presence of 2.5 mol% NaOtBu at 140 °C. Under these conditions, the catalytic β-alkylation of alcohols proceeded with high yields (up to 89%) and unprecedented turnovers (ca. 8900). Mechanistic studies are indicative of the involvement of catalysts based on in situ generated molecular Co complexes of alcohols. Labelling studies provide key evidence for the involvement of C-H activation in the cobaltous chloride catalyzed β-alkylation with a KIE of 1.61. Kinetic studies indicate linear dependence of the rate on the concentration of cobaltous chloride and sodium t-butoxide along with a non-linear dependence on the concentration of 1-phenyl ethanol and benzyl alcohol.

Phosphine-free pincer-ruthenium catalyzed biofuel production: High rates, yields and turnovers of solventless alcohol alkylation

Phosphine-free pincer-ruthenium carbonyl complexes based on bis(imino)pyridine and 2,6-bis(benzimidazole-2-yl) pyridine ligands have been synthesized. For the β-alkylation of 1-phenyl ethanol with benzyl alcohol at 140 °C under solvent-free conditions, (Cy2NNN)RuCl2(CO) (0.00025 mol%) in combination with NaOH (2.5 mol%) was highly efficient (ca. 93% yield, 372?000 TON at 12?000 TO h-1). These are the highest reported values hitherto for a ruthenium based catalyst. The β-alkylation of various alcohol combinations was accomplished with ease which culminated to give 380?000 TON at 19?000 TO h-1 for the β-alkylation of 1-phenyl ethanol with 3-methoxy benzyl alcohol. DFT studies were complementary to mechanistic studies and indicate the β-hydride elimination step involving the extrusion of acetophenone to be the overall RDS. While the hydrogenation step is favored for the formation of α-alkylated ketone, the alcoholysis step is preferred for the formation of β-alkylated alcohol. The studies were extended for the upgradation of ethanol to biofuels. Among the pincer-ruthenium complexes based on bis(imino)pyridine, (Cy2NNN)RuCl2(CO) provided high productivity (335 TON at 170 TO h-1). Sterically more open pincer-ruthenium complexes such as (Bim2NNN)RuCl2(CO) based on the 2,6-bis(benzimidazole-2-yl) pyridine ligand demonstrated better reactivity and gave not only good ethanol conversion (ca. 58%) but also high turnovers (ca. 2100) with a good rate (ca. 710 TO h-1). Kinetic studies indicate first order dependence on concentration of both the catalyst and ethanol. Phosphine-free catalytic systems operating with unprecedented activity at a very low base loading to couple lower alcohols to higher alcohols of fuel and pharmaceutical importance are the salient features of this report. This journal is

Mn(ii)-catalysed alkylation of methylene ketones with alcohols: Direct access to functionalised branched products

Herein an operationally simple alkylation of methylene ketones with primary alcohols is reported. Use of an inexpensive and earth abundant Mn/1,10-phenanthroline system enables direct access to a series of functionalised branched ketones including one-pot sequential double alkylation and Alzheimer's drug donepezil. Preliminary mechanistic investigation, determination of the rate and order of reactions and deuterium labeling experiments support the participation of the hydrogen-borrowing strategy for the ketone alkylation.

CuI/H2/NaOH-catalyzed cross-coupling of two different alcohols for carbon-carbon bond formation: "Borrowing hydrogen"?

Not borrowed: A new method was developed for the cross-coupling of two different alcohols (see scheme). This carbon-carbon bond formation was realized by using a small amount of CuBr (0.05-0.2 mol %) and NaOH (4-20 mol %) in the presence of H2 (1 atm), and provides an alternative procedure for longer-chain alcohols. The catalytic cycle was different from those reported to date for the Guerbet reaction involving "borrowing hydrogen". Copyright

Ruthenium-catalyzed redox isomerization/transfer hydrogenation in organic and aqueous media: A one-pot tandem process for the reduction of allylic alcohols

The hexamethylbenzene-ruthenium(ii) dimer [{RuCl(μ-Cl) (η6-C6Me6)}2] 1 and the mononuclear bis(allyl)-ruthenium(iv) complex [RuCl2(η 3:η2:η3-C12H 18)]2, associated with base and a hydrogen donor, were found to be active catalysts for the selective reduction of the CC bond of allylic alcohols both in organic and aqueous media. The process, which proceeds in a one-pot manner, involves a sequence of two independent reactions: (i) the initial redox-isomerization of the allylic alcohol, and (ii) subsequent transfer hydrogenation of the resulting carbonyl compound. The highly efficient transformation reported herein represents, not only an illustrative example of auto-tandem catalysis, but also an appealing alternative to the classical transition-metal catalyzed CC hydrogenations of allylic alcohols. The process has been successfully applied to aromatic as well as aliphatic substrates affording the corresponding saturated alcohols in 45-100% yields after 1.5-24 h. The best performances were reached using (i) 1-5 mol% of 1 or 2, 2-10 mol% of Cs2CO3, and propan-2-ol or (ii) 1-5 mol% of 1 or 2, 10-15 equivalents of NaO2CH, and water. The catalytic efficiency is strongly related to the structure of the allylic alcohol employed. Thus, in propan-2-ol, the reaction rate essentially depends on the steric requirement around the CC bond, therefore decreasing with the increasing number of substituents. On other hand, in water the transformation is favoured for primary allylic alcohols vs. secondary ones.

Ruthenium-catalyzed reduction of allylic alcohols: An efficient isomerization/transfer hydrogenation tandem process

A simple and highly efficient method for the selective reduction of the C=C bond in allylic alcohols has been developed using the ruthenium(ii) catalyst [{RuCl(μ-Cl)(η6-C6Me6)}2]. The Royal Society of Chemistry.

Application of A Recyclable Pseudoephedrine Resin in Asymmetric Alkylations on Solid Phase

A pseudoephedrine resin has been successfully employed in asymmetric alkylations on solid phase. Immobilized pseudoephedrine amides are conveniently prepared by the one-step attachment of pseudoephedrine to Merrifield resin through the hydroxyl group and subsequent acylation on nitrogen. Deprotonation and alkylation of the resin-bound amides proceeds smoothly. Ketones and alcohols are cleaved from the resin in high enantiomeric excess and moderate to good overall yield. The parallel, asymmetric solid-phase synthesis of a small library of chiral ketones and alcohols has been carried out to illustrate the utility of the approach. Finally, the pseudoephedrine resin can be conveniently recycled and utilized with no significant loss in the yield or enantiomeric excess of the products.

Reduction of Chiral Acyclic Ketones with Hydride-transfer Agents. Semiempirical Analysis of the Observed Stereoselectivity

(+/-)-2,2,6,6-tetramethyl-5-phenylheptan-3-one (1), (+/-)-4,4-dimethyl-1,3-diphenylpentan-1-one (2), (+/-)-2-methyl-1,3-diphenylpropan-1-one (3), and (+/-)-2,3,3-trimethyl-1-phenylbutan-1-one (4) have been reduced with lithium tetrahydridoaluminate (LAH),