246037-79-6

Basic information

• Product Name: (S)-3-(2-methoxy-4-methylphenyl)butanoic acid
• Synonyms: (S)-3-(2-methoxy-4-methylphenyl)butanoic acid
• CAS NO: 246037-79-6
• Molecular Weight: 208.257
• Mol File: 246037-79-6.mol

Chemical Properties

• CAS DataBase Reference: (S)-3-(2-methoxy-4-methylphenyl)butanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-(2-methoxy-4-methylphenyl)butanoic acid(246037-79-6)
• EPA Substance Registry System: (S)-3-(2-methoxy-4-methylphenyl)butanoic acid(246037-79-6)

Safety Data

• Hazardous Substances Data: 246037-79-6(Hazardous Substances Data)

Upstream product

• 71841-56-0 ethyl 3-(2-methoxy-4-methylphenyl)butanoate 
• 1313051-46-5 (R)-2-(2-methoxy-4-methylphenyl)propan-1-ol 
• 39701-08-1 2-methoxy-4-methyl-1-(prop-1-en-2-yl)benzene 
• 55919-62-5 2-(2-methoxy-4-methylphenyl)propan-1-ol 
• 323195-82-0 Ethyl (2E)-3-(2-methoxy-4-methylphenyl)but-2-enoate 
• 1195504-74-5 (E)-3-(2-methoxy-4-methylphenyl)but-2-enoic acid 
• 62155-72-0 (Z)-3-(2-methoxy-4-methylphenyl)but-2-enoic acid 
• 6921-64-8 4'-hydroxy-2'-methylacetophenone 

Downstream Products

• 217301-15-0 (3S)-3-(2-Methoxy-4-methylphenyl)butan-2-ol 
• 246037-80-9 3-(2-hydroxy-4-methyl-phenyl)-N-methoxy-N-methyl-butyramide 
• 131651-38-2 (S)-6-(2-hydroxy-4-methylphenyl)-2-methylhept-2-en-4-one 

Relevant articles and documents

Diastereoselective hydrogenation of α,β-unsaturated but-2-enamides to access the chiral 3-(p-tolyl) butanoic acids

An alternative methodology for the synthesis of chiral 3-(p-tolyl) butanoic acids is presented. This was accomplished through the diastereoselective hydrogenation reaction of different chiral N-3-(p-tolyl) but-2-enamides, using Pd/C in EtOH, to produce the corresponding chiral N-3-(p-tolyl) butanamides with high chemical yields and moderate diastereomeric ratios. Removal of the chiral auxiliary from N-3-(p-tolyl) butanamides gave the respective enantiomerically pure acids.

Lipase-mediated resolution of substituted 2-aryl-propanols: Application to the enantioselective synthesis of phenolic sesquiterpenes

A comprehensive study of the lipase-mediated resolution of substituted 2-aryl-propanols is reported. The latter alcohols were submitted to the irreversible acetylation catalyzed either by PPL, CRL, or lipase PS. The enantioselectivity of these transformations was dependent on the type of lipase used. The type of substituents and particularly their position on the aromatic ring strongly affected the selectivity of the reaction. The experiments described prove that PPL is the more versatile lipase catalyzing the acetylation with an enantiomeric ratio (E) value that ranges from 1 up to 144, depending on the substrate used. Conversely, the same transformations were catalyzed by CRL and lipase PS with an enantiomeric ratio value, which is always less than 5. The remarkable behavior of PPL was exploited in the large scale resolution of some substituted 2-aryl-propanols whose enantiomeric forms are relevant building blocks in the enantioselective synthesis of phenolic sesquiterpenes. By these means, the synthesis of (S)-turmeronol B and the formal syntheses of (R)-curcumene, (R)-curcuphenol, (R)-xanthorrhizol, and (R)-curcuhydroquinone were accomplished.

Enantioselective synthesis of (R)- and (S)-curcumene and curcuphenol: an efficient chemoenzymatic route

An efficient enantioselective synthesis of curcumene and curcuphenol is described. The key intermediates, substituted butanoates 7a and 7b and their acids 8a and 8b are obtained in high enantiopurity (>99% ee) by a lipase-catalyzed kinetic resolution proc

Use of 1,1'-binaphthalene-8,8'-diol as a chiral auxiliary for asymmetric Michael addition. Application to the syntheses of turmeronol A and B

Highly diastereoselective Michael addition of lithium diorganocuprates to the half-ester of 1,1'-binaphthalene-8,8'-diol gave β-substituted esters with high enantiomeric excess after methanolysis. The optically active phenolic sesquiterpenes turmeronol A (1) and B (2) have been synthesized using this reaction as a key step.