154148-85-3

Basic information

• Product Name: 2-(((3',4'-dimethoxyphenyl)methoxy)methyl)-6-(1'-hydroxy-1'-(5''-imidazolyl)methyl)toluene
• Synonyms: 2-(((3',4'-dimethoxyphenyl)methoxy)methyl)-6-(1'-hydroxy-1'-(5''-imidazolyl)methyl)toluene
• CAS NO: 154148-85-3
• Molecular Weight: 368.433
• Mol File: 154148-85-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-(((3',4'-dimethoxyphenyl)methoxy)methyl)-6-(1'-hydroxy-1'-(5''-imidazolyl)methyl)toluene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(((3',4'-dimethoxyphenyl)methoxy)methyl)-6-(1'-hydroxy-1'-(5''-imidazolyl)methyl)toluene(154148-85-3)
• EPA Substance Registry System: 2-(((3',4'-dimethoxyphenyl)methoxy)methyl)-6-(1'-hydroxy-1'-(5''-imidazolyl)methyl)toluene(154148-85-3)

Safety Data

• Hazardous Substances Data: 154148-85-3(Hazardous Substances Data)

Upstream product

• 529-20-4 2-methylphenyl aldehyde 
• 83647-43-2 3-bromo-2-methylbenzyl alcohol 
• 3034-50-2 5-imidazolecarboxaldehyde 
• 154148-84-2 2-((3',4'-dimethoxyphenyl)methoxy)methyl-6-bromotoluene 

Downstream Products

• 128366-51-8 2-methyl-3-(1'-methyl-1'-(5''-imidazolyl)methyl)benzoic acid 
• 154148-90-0 2-(((3',4'dimethoxyphenyl)methoxy)methyl)-6-(1'-methyl-1'-(5''-imidazolyl)methyl)toluene 
• 154148-88-6 2-(((3',4'dimethoxyphenyl)methoxy)methyl)-6-(1'-hydroxy-1'methyl-1'-(5''-imidazolyl)methyl)toluene 
• 154148-89-7 2-(((3',4'dimethoxyphenyl)methoxy)methyl)-6-(1'-methylene-1'-(5''-imidazolyl)methyl)toluene 
• 148324-04-3 methyl 2-methyl-3-(1'-methyl-1'-(5''-imidazolyl)methyl)benzoate 
• 128366-50-7 2-(hydroxymethyl)-6-(1'-methyl-1'-(5''-imidazolyl)methyl)toluene 
• 154148-87-5 2-(((3',4'dimethoxyphenyl)methoxy)methyl)-6-(1'-oxo-1'-(5''-imidazolyl)methyl)toluene 
• 154148-86-4 2-(((3',4'-dimethoxyphenyl)methoxy)methyl)-6-((5'-imidazolyl)methyl)toluene 

Relevant articles and documents

Synthesis of detomidine and medetomidine metabolites: 1,2,3- Trisubstituted arenes with 4'(5')-imidazolylmethyl groups

Two synthetic strategies permitted the synthesis of various metabolites of detomidine (1) and medetomidine (4), potent α-2 adrenoceptor agonists that undergo rapid oxidative metabolism at the aromatic methyl group distal to the imidazole ring. In the detomidine series, the addition of a Grignard reagent prepared from 2-((3',4'-dimethoxyphenyl)methoxy)methyl-6-bromotoluene (13) to imidazole-4(5)-carboxaldehyde (7) provided 2-(((3',4'- dimethoxyphenyl)methoxy)methyl)-6-(1'-hydroxy-1'-(5''- imidazolyl)methyl)toluene (14). In a subsequent reduction, it was possible to differentiate between the secondary benzylic hydroxyl group and the primary benzylic hydroxyl group protected as a 3,4-dimethoxybenzyl ether. Removal of the protecting group provided 3-(hydroxymethyl)detomidine (3-HD) (2) and an oxidation furnished 3-carboxydetomidine (3-CD) (3). However, in the medetomidine series, a similar hydrogenolysis of 2-(((3',4'- dimethoxyphenyl)methoxy)methyl)-6-(1'-hydroxy-1'-methyl-1'-(5''- imidazolyl)methyl)toluene (17) failed, and an alternate, longer route involving dehydration and reduction was necessary to secure 3- (hydroxymethyl)medetomidine (3-HM) (5) and following an oxidation, 3- carboxymedetomidine (3-CM) (6). Finally, an expeditious route to 3-CM (6) involved the addition of the Grignard reagent prepared from 2-(3-bromo-2- methylphenyl)-4,4-dimethyl-2-oxazoline (22) to 4-acetyl-1H-imidazole and the hydrogenolysis and hydrolysis of 2-(1-(4,4-dimethyl-2-oxazolyl))-6-(1'-oxo- 1'-(5'-imidazolyl)methyl)toluene (23).