7779-78-4

Usage

Uses

Used in Flavor Industry:
4-METHYL-1-PHENYL-2-PENTANOL is used as a flavoring agent for its buttery, oily, caramellic flavor, adding depth and complexity to various food and beverage products.
Used in Fragrance Industry:
4-METHYL-1-PHENYL-2-PENTANOL is used as a fragrance ingredient for its green, floral, and herbaceous scent, contributing to the creation of various perfumes, colognes, and other scented products.
Used in Chemical Synthesis:
4-METHYL-1-PHENYL-2-PENTANOL can be used as a starting material or intermediate in the synthesis of other organic compounds, such as pharmaceuticals, agrochemicals, or specialty chemicals, due to its unique structure and functional groups.

Preparation

By reacting isobutyl aldehyde with benzyl magnesium chloride.

Biochem/physiol Actions

Taste at 10 ppm

Synthesis

4-Methyl-1-phenyl-2-pentanol is prepared from benzyl chloride to benzyl magnesium bromide, and then hydrolyzed with isovaleraldehyde after Grignard reaction.

InChI:InChI=1/C12H18O/c1-10(2)8-12(13)9-11-6-4-3-5-7-11/h3-7,10,12-13H,8-9H2,1-2H3

Upstream product

• 100-44-7 benzyl chloride 
• 590-86-3 isovaleraldehyde 
• 5349-62-2 4-Methyl-1-phenyl-2-pentanone 
• 65473-82-7 2-isobutyl-3-phenyloxirane 
• 54624-34-9 (4-methylpent-1-en-1-yl)benzene 
• 100-46-9 benzylamine 
• 66310-10-9 N-benzyl-2,4,6-triphenylpyridinium tetrafluoroborate 
• 103-82-2 phenylacetic acid 
• 770-09-2 benzyltrimethylsilane 
• 122-78-1 phenylacetaldehyde 

Relevant academic research and scientific papers

C-H Alkylation of Aldehydes by Merging TBADT Hydrogen Atom Transfer with Nickel Catalysis

Catalyst controlled site-selective C-H functionalization is a challenging but powerful tool in organic synthesis. Polarity-matched and sterically controlled hydrogen atom transfer (HAT) provides an excellent opportunity for site-selective functionalization. As such, the dual Ni/photoredox system was successfully employed to generate acyl radicals from aldehydes via selective formyl C-H activation and subsequently cross-coupled to generate ketones, a ubiquitous structural motif present in the vast majority of natural and bioactive molecules. However, only a handful of examples that are constrained to the use of aryl halides are developed. Given the wide availability of amines, we developed a cross-coupling reaction via C-N bond cleavage using the economic nickel and TBADT catalyst for the first time. A range of alkyl and aryl aldehydes were cross-coupled with benzylic and allylic pyridinium salts to afford ketones with a broad spectrum of functional group tolerance. High regioselectivity toward formyl C-H bonds even in the presence of α-methylene carbonyl or α-amino/oxy methylene was obtained.

A General Regioselective Synthesis of Alcohols by Cobalt-Catalyzed Hydrogenation of Epoxides

A straightforward methodology for the synthesis of anti-Markovnikov-type alcohols is presented. By using a specific cobalt triphos complex in the presence of Zn(OTf)2 as an additive, the hydrogenation of epoxides proceeds with high yields and selectivities. The described protocol shows a broad substrate scope, including multi-substituted internal and terminal epoxides, as well as a good functional-group tolerance. Various natural-product derivatives, including steroids, terpenoids, and sesquiterpenoids, gave access to the corresponding alcohols in moderate-to-excellent yields.

Photocatalytic carbanion generation-benzylation of aliphatic aldehydes to secondary alcohols

We present a redox-neutral method for the photocatalytic generation of carbanions. Benzylic carboxylates are photooxidized by single electron transfer; immediate CO2 extrusion and reduction of the in situ formed radical yields a carbanion capable of reacting with aliphatic aldehydes as electrophiles giving the Grignard analogous reaction product.

Screening on the use of Kluyveromyces marxianus CBS 6556 growing cells as enantioselective biocatalysts for ketone reductions

The versatility of Kluyveromyces marxianus CBS 6556 growing cells in the enantioselective reduction of ketone functionalities to the corresponding alcohols was exploited. In particular, methyl ketones were reduced to (S)-alcohols with ees of up to 96%. Longer chain alkyl ketones afforded, under the same experimental condition, (R)-alcohols with an ee of up to 84%. Interestingly, carbon-carbon double and the triple bonds can also be reduced in the presence of Kluyveromyces marxianus CBS 6556 yeast. A cyclic ketone, such as 2-tetralone, was also quantitatively reduced to its corresponding (S)-alcohol with ee = 76%.

Le benzyltrimethylsilane, un agent pratique de benzylation

In the presence of Bu4N(1+))*F(1-), benzyltrimethylsilane behaves as a convenient benzylation reagent.In the reaction with non conjugated aldehydes, pehenethylalcohols are obtained in satisfactory yields upon hydrolysis, while the formation of bibenzyl or ortho products are not observed.When the reaction occurs with α,β-unsaturated aldehydes and ketones, only 1,2-addition is observed even in the case of chalcone.

UN NOVEAU SYNTHON ORGANOSILICIE: LE BENZYLTRIMETHYLSILANE

In the presence of tetrabutylammonium fluoride (TBAF) as the catalyst, benzyltrimethylsilane adds to aldehydes and ketones to afford, upon hydrolysis, the corresponding alcohols.The use of PhCH2SiMe3 as a general benzylation reagent is here reported for the first time.