100760-03-0

Usage

Uses

Used in Fragrance Industry:
(1R)-1-(3,4-dimethylphenyl)ethanol is used as a fragrance ingredient for its pleasant scent. It is commonly incorporated into perfumes and colognes due to its sweet floral aroma, enhancing the overall fragrance experience.
Used in Cosmetic and Personal Care Industries:
(1R)-1-(3,4-dimethylphenyl)ethanol is utilized in the cosmetic and personal care industries as a fragrance ingredient. Its sweet floral aroma adds a desirable scent to various products, making them more appealing to consumers.
Used in Pharmaceutical Production:
(1R)-1-(3,4-dimethylphenyl)ethanol is also used in the production of pharmaceuticals. Its unique properties make it a valuable component in the development of certain medications.
Used in Flavor and Food Products:
Additionally, (1R)-1-(3,4-dimethylphenyl)ethanol can be found in some flavors and food products, where it contributes to the overall taste and aroma profile, providing a pleasant sensory experience for consumers.
It is important to follow proper handling and storage procedures for (1R)-1-(3,4-dimethylphenyl)ethanol to ensure its safe and effective use in various applications.

Upstream product

• 3637-01-2 3,4-dimethylacetophenone 
• 108-05-4 vinyl acetate 
• 33967-19-0 1-(3,4-dimethylphenyl)ethanol 
• 100646-19-3 1-(3',4'-dimethylphenyl)ethyl hydrogen phthalate 

Downstream Products

• 20871-94-7 (+)-1-(3',4'-dimethylphenyl)bromoethane 

Relevant academic research and scientific papers

Cobalt-catalyzed asymmetric hydrogenation of ketones: A remarkable additive effect on enantioselectivity

A chiral cobalt pincer complex, when combined with an achiral electron-rich mono-phosphine ligand, catalyzes efficient asymmetric hydrogenation of a wide range of aryl ketones, affording chiral alcohols with high yields and moderate to excellent enantioselectivities (29 examples, up to 93% ee). Notably, the achiral mono-phosphine ligand shows a remarkable effect on the enantioselectivity of the reaction.

Facile development of chiral alkenylboranes from chiral diynes for asymmetric hydrogenation of silyl enol ethers

A facile development of chiral alkenylboranes by the hydroboration of chiral diynes with Piers borane was successfully achieved for the first time. With the combination of the in situ generated chiral alkenylboranes and tri-tert-butylphosphine as frustrated Lewis pair catalysts, the metal-free asymmetric hydrogenation of silyl enol ethers was realized to furnish a wide range of optically active secondary alcohols in high yields and up to 99% ee.

A highly enantioselective hydrogenation of silyl enol ethers catalyzed by chiral frustrated lewis pairs

Using a simple combination of tri-tert-butylphosphine and chiral borane generated in situ by the hydroboration of chiral diene with HB(C 6F5)2 as a frustrated Lewis pair catalyst, a highly enantioselective metal-free hydrogenation of silyl enol ethers was successfully realized to furnish a variety of optically active secondary alcohols in 93-99% yields with 88->99% ees.

Chiral Oxazolidine-Fused N-Heterocyclic Carbene Complexes of Rhodium and Iridium and Their Utility in the Asymmetric Transfer Hydrogenation of Ketones

The catalytic potential of new N-heterocyclic carbene ligands, derived from a chiral fused bicyclic ring scaffold with restricted rotation along the C–N bond bearing the chiral auxiliary, has been explored in the transition-metal-mediated asymmetric transfer hydrogenation reactions of ketones. In particular, the chiral oxazolidine-fused N-heterocyclic carbene precursors (3S)-3-R-6-methyl-7-phenyl-2,3-dihydroimidazo[5,1-b]oxazol-6-ium iodide [R = sec-butyl (1f), i-butyl (2f), isopropyl (3f)] were synthesized from commercially available optically pure amino acids in a multistep sequence that avoids tedious chiral resolution. The reactions of the chiral imidazolium iodide salts 1f–3f with Ag2O yielded the corresponding silver complexes 1g–3g, which were treated with [(COD)MCl]2 (M = Rh, Ir; COD = 1,5-cyclooctadiene) to afford the rhodium(I) and iridium(I) complexes (1h–3h and 1i–3i, respectively). The rhodium(I) and iridium(I) complexes conveniently catalyze the asymmetric transfer hydrogenation of acetophenones for a wide variety of substrates ranging from electron-rich ones such as 4-methylacetophenone, 3,4-dimethylacetophenone, 4-tert-butylacetophenone, and 4-(methylthio)acetophenone to electron-deficient ones such as 4-bromoacetophenone, 4-chloroacetophenone, 4-fluoroacetophenone, 4-nitroacetophenone, and 3-fluoroacetophenone in moderate-to-good yields (ca. 18–95 %) but with low enantioselectivities (ca. 4–41 % ee).

Escherichia coli BioH: A highly enantioselective and organic solvent tolerant esterase for kinetic resolution of sec-alcohols

Escherichia coli BioH, which is obligatory for biotin synthesis, was found to be an organic solvent tolerant esterase with high enantioselectivity for the kinetic resolution of sec-alcohols using free enzyme powder. With this esterase, a variety of racemic sec-alcohols were efficiently resolved with ee values of up to 99%.

Chiral Frustrated Lewis Pairs Catalyzed Highly Enantioselective Hydrosilylations of Ketones

A highly enantioselective Piers-type hydrosilylation of simple ketones was successfully realized using a chiral frustrated Lewis pair of tri-tert-butylphosphine and chiral diene-derived borane as catalyst. A wide range of optically active secondary alcohols were furnished in 80%—99% yields with 81%—97% ee's under mild reaction conditions.

Plant-mediated asymmetric reduction of 1-(3,4-dimethylphenyl)ethanone

Bioreduction mediated by plants is a highly selective and environmentally friendly approach to synthesise optically active alcohols. Herein the bioreduction of 1-(3,4)-dimethylphenyl)ethanone to the corresponding chiral alcohol 1-(3,4-dimethylphenyl)ethanol has been evaluated using nine different vegetables roots as biocatalysts. The chiral alcohol was prepared in yields ranging from 44.1% to 88.2%, and with enantiomeric excess up to 97.2% for the (S)-enantiomer. Sugar beet was the most promising among the tested vegetables roots. Therefore, sugar beet cell cultures (normal and transformed) were obtained and tested for the reduction as well, yielding the corresponding alcohol in the range from 62.1% to 88.2% yield and with enantiomeric excesses of >99%. Based on these results reported, there are no profound differences in the reductive capacity of undifferentiated cells and organs of the same plant species (sugar beet). Due to overall advantages of using cell cultures, we have highlighted this approach as a promising method for preparation of enantiomerically pure 1-(3,4-dimethylphenyl)ethanol.

New paracyclophane phosphine for highly enantioselective ruthenium-catalyzed hydrogenation of prochiral ketones

The synthesis of a new paracyclophane phosphine is described. This ligand was highly efficient in the ruthenium-catalyzed asymmetric hydrogenation of various aromatic and heteroaromatic ketones. Georg Thieme Verlag Stuttgart.

Preparation of chiral 1-phenylethanols and bromides

A fast, convenient procedure for preparing and resolving moderate to large quantities of chiral secondary alcohols is described.The general procedure involves a one-pot conversion of the ketone (various acetophenones) to the half-ester of a diacid (succinic, phthalic...) and resolution with (+)- and (-)-1-phenylethylamines.Overall yields of the enantiomeric alcohols, the variously substituted 1-phenylethanols, are generally 65-85percent with optical purities of approximately 90percent.Properties and optical rotations of a number of chiral 1-phenylethanols and of the bromides made from them are tabulated.A discussion of optical purity determinations using nmr methods is included and absolute configurations are reported.