74408-48-3

Upstream product

• 18713-58-1 1-(4-chlorophenyl)-2-methylpropan-1-one 
• 201230-82-2 carbon monoxide 
• 19366-15-5 4-chloro-β,β-dimethylstyrene 
• 51631-50-6 2-(4-chlorophenyl)-3-methyl-(2SR)-butanoyl chloride 
• 65079-44-9 2-(4-Chlorophenyl)-3-methyl-1-butanol 

Downstream Products

• 2012-74-0 2-(4-chlorophenyl)-3-methylbutyric acid 
• 246233-80-7 (Z)-4-(4-Chloro-phenyl)-2-fluoro-5-methyl-hex-2-en-1-ol 
• 55332-38-2 S-isopropyl-4-chlorophenylacetic acid 
• 306974-39-0 (S)-3-methyl-2-(4-chlorophenyl)butan-1-ol 
• 246233-70-5 (Z)-4-(4-Chloro-phenyl)-2-fluoro-5-methyl-hex-2-enoic acid methyl ester 

Relevant academic research and scientific papers

Ru-catalyzed asymmetric hydrogenation of racemic aldehydes via dynamic kinetic resolution: Efficient synthesis of optically active primary alcohols

A highly efficient asymmetric hydrogenation of racemic α-arylaldehydes via dynamic kinetic resolution has been developed by using [RuCl2(SDPs)(diamine)] complexes as catalysts, providing chiral primary alcohols in excellent enantioselectivities. Copyright

A Rearrangement Route to Fenvaleric Acid

(±)-Fenvaleric acid 2, the key intermediate for the preparation of the pesticide esfenvalerate 1, was prepared by a novel sequence which first involves the Henry reaction of 2-methyl-1-nitropropane and 4-chlorobenzaldehyde. The nitroaldol reaction provided nitroalcohol 5 which was then reduced to the corresponding aminoalcohol 6. Submission of 6 to an aminopinacol rearrangement promoted by nitrous acid deamination then afforded aldehyde 8 through a 1,2-aryl shift. The product fenvaleric aldehyde 8 was then converted to the title compound 2 by a modified Jones oxidation.

Studies on the synthesis of chiral 2-(p.chlorophenyl)-3-methylbutanoic acid, a key-precursor of Fenvalerate, by hydrocarbonylation reactions

The preparation of racemic 2-(p.chlorophenyl)-3-methylbutanoic acid (2), a building block for (S,S)-Fenvalerate (an important broad spectrum insecticide), was effected by rhodium catalyzed hydroformylation of 2-methyl-1 -(p.chlorophenyl) propene (4) in the presence of excess of triphenylphosphine to inhibit substrate isomerization followed by mild oxidation of the resulting aldehyde 6; an overall yield of 88% was reached. Olefin 4 exhibits a very low tendency to undergo both hydrocarboethoxylation and hydrocarboxylation in the presence of palladium complexes as catalysts. Enantioselective hydrocarbonylation reactions carried out on olefin 4 afford unsatisfactory chemical and optical yields of the optically active ester 5 or acid 2. Springer-Verlag 1996.

Oxidation of Primary and Secondary Alcohols by the Catalysis of Palladium

Saturated and unsaturated alcohols are oxidized to the corresponding ketones in good or excellent yields by using an aryl halide (phenyl bromide or mesityl bromide) as an oxidant and palladium(0) or -(II) as a catalyst (0.6-3 mol percent relative to the alcohol) in the presence of a base (NaH or K2CO3).The similar oxidation of primary alcohols provides the corresponding aldehydes and/or esters.The aldehyde/ester selectivity is correlated to the steric and electronic features of substrates.The procedure is applied to the oxidation of 1-primary,ω-primary diols to lactones.

Metal-assisted Reactions. Part 8. Selectivity in the Reaction of Organic Halides with Tetrahydroborate and the Reduction of Acyl Halides to Aldehydes

Addition of metal ions such as Cu+, Cu2+, Cd2+, and Zn2+ with dimethylformamide to sodium tetrahydroborate in acetonitrile affords a reducing medium in which acyl halides are converted to aldehydes but alkyl, aryl, and benzylic halides are unaffected.The inertness of these last, synthetically useful, functional groups along with the inertness of other potentially reducible groups, makes the reagent very selective for direct reduction of acyl halides to aldehydes.The reducing solution is stable, readily prepared from cheap materials, rapid in action, and easy to use, making the conversion of acids to aldehydes via acyl halides a routine synthetic procedure.