67952-38-9

Usage

Uses

Used in Fragrance Production:
4-(p-methoxyphenyl)butan-2-ol is used as a key ingredient in the production of fragrances for its distinct, slightly sweet scent. It contributes to the creation of various fragrances used in personal care products, perfumes, and other scented items.
Used as a Flavoring Agent in the Food Industry:
In the food industry, 4-(p-methoxyphenyl)butan-2-ol is employed as a flavoring agent to enhance the taste and aroma of various food products. Its sweet odor adds a pleasant flavor profile to a range of consumables.
Used in Pharmaceutical Synthesis:
4-(p-methoxyphenyl)butan-2-ol is utilized in the synthesis of pharmaceuticals, serving as a valuable precursor in the development of new drugs. Its unique chemical structure allows it to be a building block for creating various medicinal compounds.
Used as a Precursor in Organic Chemistry:
In the field of organic chemistry, 4-(p-methoxyphenyl)butan-2-ol is used as a precursor for the synthesis of other organic compounds. Its versatility in chemical reactions makes it a valuable component in the creation of a wide array of chemical products.
Safety Precautions:
It is important to handle 4-(p-methoxyphenyl)butan-2-ol with care, as it can be harmful if ingested, inhaled, or comes into contact with the skin. Proper safety measures should be taken during its production, use, and disposal to minimize potential health risks.

InChI:InChI=1/C11H16O2/c1-9(12)3-4-10-5-7-11(13-2)8-6-10/h5-9,12H,3-4H2,1-2H3

Upstream product

• 104-20-1 4-(4-methoxyphenyl)-2-butanone 
• 69617-84-1 rac-rhododendrol 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 23304-25-8 p-methoxyphenyldiazomethane 
• 67-63-0 isopropyl alcohol 
• 64-17-5 ethanol 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 3815-30-3 4-(4-methoxyphenyl)-3-buten-2-one 
• 943-88-4 4-(p-methoxyphenyl)-3-butene-2-one 
• 67-64-1 acetone 
• 55831-55-5 1-isoprenyloxymethyl-4-methoxybenzene 
• 134747-45-8 4-(4-methoxyphenyl)-3-buten-2-ol 
• 152339-86-1 (S)-4-(4′-methoxyphenyl)-2-butanol 

Downstream Products

• 10528-67-3 4-cyclohexyl-2-butanol 
• 100-09-4 4-methoxybenzoic acid 
• 104-20-1 4-(4-methoxyphenyl)-2-butanone 
• 152339-86-1 (S)-4-(4′-methoxyphenyl)-2-butanol 
• 39516-05-7 (R)-4-(4′-methoxyphenyl)-2-butanol 
• 39831-53-3 1-(but-2-en-1-yl)-4-methoxybenzene 
• 20574-98-5 4-(p-methoxyphenyl)but-1-ene 
• 126521-63-9 4-(4-methoxyphenyl)butan-2-yl 4-methylbenzenesulfonate 
• 344791-87-3 (rac)-4-(3-bromobutyl)-1-methoxybenzene 
• 1383841-51-7 (rac)-1-methoxy-4-(3-phenylbutyl)benzene 
• 1383841-50-6 1-(3-iodo-butyl)-4-methoxy-benzene 
• 1338073-35-0 2-(4-(4-methoxyphenyl)butan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

Interrupting the Barton?McCombie reaction: Aqueous deoxygenative trifluoromethylation of o-alkyl thiocarbonates

The site-selective trifluoromethylation of aliphatic systems remains an important challenge. This work describes a light-driven, copper-mediated trifluoromethylation of O-alkyl thiocarbonates. The reaction provides broad functional group tolerance (e.g., alkyne, alkene, phenol, free alcohol, electron-rich and -deficient arenes), thereby offering orthogonality and practicality for trifluoromethylation. A radical organometallic mechanism is proposed.

Deracemization and Stereoinversion of Alcohols Using Two Mutants of Secondary Alcohol Dehydrogenase from Thermoanaerobacter pseudoethanolicus

We developed a one-pot sequential two-step deracemization approach to chiral alcohols using two mutants of Thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase (TeSADH). This approach relies on consecutive non-stereospecific oxidation of alcohols and stereoselective reduction of their prochiral ketones using two mutants of TeSADH with poor and good stereoselectivities, respectively. More specifically, W110G TeSADH enables a non-stereospecific oxidation of alcohol racemates to their corresponding prochiral ketones, followed by W110V TeSADH-catalyzed stereoselective reduction of the resultant ketone intermediates to enantiopure (S)-configured alcohols in up to > 99 percent enantiomeric excess. A heat treatment after the oxidation step was required to avoid the interference of the marginally stereoselective W110G TeSADH in the reduction step; this heat treatment was eliminated by using sol-gel encapsulated W110G TeSADH in the oxidation step. Moreover, this bi-enzymatic approach was implemented in the stereoinversion of (R)-configured alcohols, and (S)-configured alcohols with up to > 99 percent enantiomeric excess were obtained by this Mitsunobu-like stereoinversion reaction.

Selective Cross-Dehydrogenative C(sp3)-H Arylation with Arenes

Selective C(sp3)-C(sp2) bond construction is of central interest in chemical synthesis. Despite the success of classic cross-coupling reactions, the cross-dehydrogenative coupling between inert C(sp3)-H and C(sp2)-H bonds represents an attractive alternative toward new C(sp3)-C(sp2) bonds. Herein, we establish a selective inter-and intramolecular C(sp3)-H arylation of alcohols with nondirected arenes that thereby provides a general pathway to access a wide range of β-arylated alcohols, including tetrahydronaphthalen-2-ols and benzopyran-3-ols, with high to excellent chemo-and regioselectivity.

Iron-catalyzed protodehalogenation of alkyl and aryl halides using hydrosilanes

A simple and efficient iron-catalyzed protodehalogenation of alkyl and aryl halides using phenylhydrosilane is disclosed. The reaction utilizes FeCl3 without the requirement of ligands. Unactivated alkyl and aryl halides were successfully reduced in good yields; sterically hindered tertiary halides were also reduced including the less reactive chlorides. The scalability of this methodology was demonstrated by a gram-scale synthesis with a catalyst loading as low as 0.5 mol%. Notably, disproportionation of phenylsilane leads to diphenylsilane that further reduces the halides. Preliminary mechanistic studies revealed a non-radical pathway and the source of hydrogen is PhSiH3via deuterium labeling studies. Our methodology represents simplicity and provides a good alternative to typical tin, aluminum and boron hydride reagents.

Ti-Catalyzed Radical Alkylation of Secondary and Tertiary Alkyl Chlorides Using Michael Acceptors

Alkyl chlorides are common functional groups in synthetic organic chemistry. However, the engagement of unactivated alkyl chlorides, especially tertiary alkyl chlorides, in transition-metal-catalyzed C-C bond formation remains challenging. Herein, we describe the development of a TiIII-catalyzed radical addition of 2° and 3° alkyl chlorides to electron-deficient alkenes. Mechanistic data are consistent with inner-sphere activation of the C-Cl bond featuring TiIII-mediated Cl atom abstraction. Evidence suggests that the active TiIII catalyst is generated from the TiIV precursor in a Lewis-acid-assisted electron transfer process.

Expanding the Substrate Specificity of Thermoanaerobacter pseudoethanolicus Secondary Alcohol Dehydrogenase by a Dual Site Mutation

Here, we report the asymmetric reduction of selected phenyl-ring-containing ketones by various single- and dual-site mutants of Thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase (TeSADH). The further expansion of the size of the substrate binding pocket in the mutant W110A/I86A not only allowed the accommodation of substrates of the single mutants W110A and I86A within the expanded active site but also expanded the substrate range of the enzyme to ketones bearing two sterically demanding groups (bulky–bulky ketones), which are not substrates for the TeSADH single mutants. We also report the regio- and enantioselective reduction of diketones with W110A/I86A TeSADH and single TeSADH mutants. The double mutant exhibited dual stereopreference to generate the Prelog products most of the time and the anti-Prelog products in a few cases.

Nickel-Catalyzed C-Alkylation of Nitroalkanes with Unactivated Alkyl Iodides

Enabled by nickel catalysis, a mild and general catalytic method for C-alkylation of nitroalkanes with unactivated alkyl iodides is described. Compatible with primary, secondary, and tertiary alkyl iodides; and tolerant of a wide range of functional groups, this method allows rapid access to diverse nitroalkanes.

Cobalt-Catalyzed Silylcarbonylation of Unactivated Secondary Alkyl Tosylates at Low Pressure

A catalytic preparation of silyl enol ethers from unactivated secondary alkyl tosylates is reported. An inexpensive cobalt catalyst is used under mild conditions with low pressures of carbon monoxide. Nucleophilic, anionic cobalt carbonyls facilitate the catalytic activation of a range of alkyl tosylates. The silylcarbonylation offers a practical approach to synthetically valuable silyl enol ethers from simple starting materials.

Multifunctional supported bimetallic catalysts for a cascade reaction with hydrogen auto transfer: Synthesis of 4-phenylbutan-2-ones from 4-methoxybenzyl alcohols

We report the one-pot tandem synthesis of 4-(4-methoxyphenyl)butan-2-one directly from 4-methoxybenzyl alcohol and acetone using a multifunctional supported AuPd nanoalloy catalyst. This one-pot synthesis involves dehydrogenation, aldol condensation and hydrogenation of CC. In this supported AuPd catalyst, the bimetallic sites catalyse the dehydrogenation and hydrogenation steps and, in combination with the support, catalyse the C-C coupling (aldol) process. This supported bimetallic catalyst is also effective in utilizing hydrogen from the dehydrogenation reaction for the hydrogenation of 4-(4-methoxyphenyl)but-3-en-2-one to 4-(4-methoxyphenyl)butane-2-one via a hydrogen auto transfer route. These multifunctional catalysts were characterised using transmission electron microscopy, X-ray diffraction and X-ray photoelectron spectroscopy.

Manganese-Catalyzed Borylation of Unactivated Alkyl Chlorides

The use of low-cost manganese(II) bromide (MnBr2) and tetramethylethylenediamine (TMEDA) catalyzes the cross coupling of (bis)pinacolatodiboron with a wide range of alkyl halides, demonstrating the first manganese-catalyzed coupling with alkyl electrophiles. This method allows access to primary, secondary, and tertiary boronic esters from the parent chlorides, which were previously inaccessible as coupling partners. The reaction proceeds in high yield with as little as 1000 ppm catalyst loading, while 5 mol % can provide high yields in as little as 30 min. Finally, radical-clock experiments revealed that at 0 °C direct borylation outcompetes alternative radical processes, thereby providing synthetically useful, temperature-controlled reaction outcomes.