55262-10-7

Upstream product

• 118-90-1 ortho-methylbenzoic acid 
• 74-88-4 methyl iodide 
• 55262-06-1 methyl 1,2-dimethylcyclohexa-2,5-diene-1-carboxylate 
• 74-83-9 methyl bromide 

Downstream Products

• 115513-41-2 (1,2-Dimethyl-cyclohexa-2,5-dienyl)-((S)-2-hydroxymethyl-pyrrolidin-1-yl)-methanone 
• 95-47-6 o-xylene 
• 464-72-2 tetraphenylethane-1,2-diol 
• 1334440-49-1 4,5-dimethyl-1,2-dihydro-1,1'-biphenyl 
• 99583-84-3 (1,2-Dimethyl-cyclohexa-2,5-dienyl)-((S)-2-methoxymethyl-pyrrolidin-1-yl)-methanone 
• 55262-06-1 methyl 1,2-dimethylcyclohexa-2,5-diene-1-carboxylate 

Relevant academic research and scientific papers

Synthesis of precursors of phomactins using [2,3]-Wittig rearrangements

o-Toluic acid has been converted into methyl (8RS,9SR)-7-(bromomethyl)-8,9-dimethyl-1,4-dioxaspiro[4.5]dec-6-ene-8-carboxylate, the stereochemical defining step being a conjugate addition of lithium dimethylcuprate to a cyclohexadienone prepared using a B

Regioselective arene functionalization: Simple substitution of carboxylate by alkyl groups

Arenes with various alkyl side-chains were synthesized in high yields and excellent regioselectivities. Starting from toluic and naphthoic acids, the carboxylate group was conveniently substituted by alkyl halides by Birch reduction and subsequent decarbonylation. The method is characterized by inexpensive starting materials and reagents, and methylation of arenes was realized. Besides simple alkyl substituents, the scope of arene functionalization was extended by benzyl, fluoro, amino, and ester groups. We were able to control the alkylation of 1-naphthoic acid during Birch reduction by the addition of tert-butanol. This allowed the regioselective synthesis of mono and bis-substituted naphthalenes from the same starting material.

Simple two-step ipso substitution of aromatic carboxylic acids by alkyl halides

Methyl-substituted arenes can be synthesized with high regioselectivity in only two steps through formal exchange of an aromatic carboxylic acid function with an alkyl substituent. The results obtained with toluic acid illustrate that good to very good yields can be obtained from inexpensive reagents (see scheme).

Approaches to the total synthesis of phomactins

The macrocyclic triene 34, an advanced intermediate for synthesis of phomactins, has been synthesized using the 2,3-Wittig rearrangement of the propargylic ether 21 as a key step.

THE ENANTIOSELECTIVE CONVERSION OF ORTHO-SUBSTITUTED BENZOIC ACIDS TO CHIRAL CYCLOHEXANE DERIVATIVES

The diastereoselectivity of reductive methylation of 1a-1c to give 2a-2c and 11 to give 12 is 260:1 and >99:1, respectively.