201359-55-9

Upstream product

• 93-51-6 2-Methoxy-4-methylphenol 
• 106-95-6 allyl bromide 
• 121-33-5 vanillin 

Downstream Products

• 77879-82-4 2-allyl-4-methyl-6-methoxyphenol 
• 6270-23-1 2-(2-methoxy-4-methylphenoxy)acetic acid 
• 16766-16-8 (2-methoxy-4-methylphenoxy)acetaldehyde 
• 93-51-6 2-Methoxy-4-methylphenol 
• 1064703-80-5 C₁₁H₁₃⁽²⁾HO₂ 
• 5653-56-5 2,3-dimethoxy-5-methylbenzoic acid 
• 369362-35-6 2-(2,3-dimethoxy-5-methyl-phenyl)-2-methyl-pent-4-enoic acid methyl ester 
• 369362-37-8 2-(2,3-dimethoxy-5-methyl-phenyl)-2-methyl-4-oxo-pentanal 
• 369362-38-9 4-(2,3-dimethoxy-5-methyl-phenyl)-4-methyl-cyclopent-2-enone 
• 369362-36-7 2-(2,3-dimethoxy-5-methyl-phenyl)-2-methyl-pent-4-enal 
• 96202-91-4 (2,3-dimethoxy-5-methyl-phenyl)-acetic acid methyl ester 
• 369362-34-5 2-(2,3-dimethoxy-5-methyl-phenyl)-propionic acid methyl ester 
• 369362-33-4 (2,3-dimethoxy-5-methyl-phenyl)-acetaldehyde 
• 369362-32-3 1-allyl-2,3-dimethoxy-5-methyl-benzene 

Relevant academic research and scientific papers

Boosting effect of ortho-propenyl substituent on the antioxidant activity of natural phenols

Seven new antioxidants derived from natural or synthetic phenols have been designed as alternatives to BHT and BHA antioxidants. Influence of various substituents at the ortho, meta and para positions of the aromatic core of phenols on the bond dissociation enthalpy of the ArO-H bond was evaluated using a DFT method B3LYP/6-311++G(2d,2p)//B3LYP/6-311G(d,p). This prediction highlighted the ortho-propenyl group as the best substituent to decrease the bond dissociation enthalpy (BDE) value. The rate constants of hydrogen transfer from these phenols to DPPH radical in a non-polar and non-protic solvent have been measured and were found to be in agreement with the BDE calculations. For o-propenyl derivatives from 2-tert-butyl-4-methylphenol, BHA, creosol, isoeugenol and di-o-propenyl p-cresol, fewer radicals were trapped by a single phenol molecule, i.e. a lower stoichiometric number. Reaction mechanisms involving the evolution of the primary phenoxyl radical ArO are proposed to rationalise these effects.

Structure-activity relationships in the domain of odorants having marine notes

Continuing our investigations into marine note odorants, we herein describe several new scaffolds. Among them, 2,3-dihydrobenzofuran-2-carbaldehyde is particularly interesting. The results demonstrate that the seven-membered ring with a ketone functional group of the Calone 1951 family can be replaced by a five-membered ring carrying an aldehydefunction. In addition, this work has allowed us to discover the valuable 2-methoxy-4-methylphenyl methyl carbonate (20b), which is very close to vanillin, and 2-methoxy-2,4-dimethyl-1,3-benzodioxole (29d), which belongs to the isoeugenol/dihydroeugenol olfactive family.

Synthesis of the landomycinone skeleton

The synthesis of the highly functionalized tetracyclic skeleton of landomycinone (2), the aglycon of landomycins, was performed using two pivotal steps relying on metal-catalyzed reactions. They are (1) a [2 + 2 + 2] cycloaddition of alkynes promoted by W

Selective O-deallylation of o-allyloxyanisoles

o-Allyloxyanisoles are selectively and easily deallylated by treatment with sec- or tert-butyllithium at low temperature. The reaction is proposed to proceed through a tandem intermolecular carbolithiation-β;-elimination process, which can also be considered an SN2′ attack of the organolithium on the allyl ether.

Total synthesis of (±)-herbertenediol

A formal total synthesis of the sesquiterpene (±)-herbertenediol and its dimers mastigophorenes A-D has been accomplished, starting from vanillin via 2,3-dimethoxy-5-methylbenzaldehyde. A combination of Claisen rearrangement and ring-closing metathesis reactions were employed for the generation of the two vicinal quaternary carbons on a cyclopentane ring.

Synthesis of chiral chromans by the Pd-catalyzed asymmetric allylic alkylation (AAA): Scope, mechanism, and applications

The Pd-catalyzed asymmetric allylic alkylation (AAA) of phenol allyl carbonates serves as an efficient strategy to construct the allylic C-O bond allowing access to chiral chromans in up to 98% ee. The effect of pH and the influence of olefin geometry, as well as substitution pattern on the ee and the absolute configuration of the chiral chromans were explored in detail. These observations suggest a mechanism involving the cyclization of the more reactive π-allyl palladium diastereomeric intermediate as the enantiodiscriminating step (Curtin-Hammett conditions). This methodology led to the enantioselective synthesis of the vitamin E core, the first enantioselective total synthesis of (+)-clusifoliol and (-)-siccanin, and the synthesis of an advanced intermediate toward (+)-rhododaurichromanic acid A.

Formal total synthesis of (±)-herbertenediol and (±)-mastigophorenes A and B

A simple and straightforward formal total synthesis of the sesquiterpene herbertenediol and its dimers mastigophorenes A and B, starting from vanillin, is described.