2242-35-5

Upstream product

• 2242-34-4 Benzoesaeure-<2-benzyloxy-5-nitro-phenylester> 
• 2620-44-2 5-nitro-1,3-benzodioxole 
• 20194-18-7 sodium phenyl-methanolate 
• 100-51-6 benzyl alcohol 
• 5876-96-0 2-Benzoyloxy-4-nitro-phenol 
• 3316-09-4 1,2-dihydroxy-4-nitrobenzene 
• 100-39-0 benzyl bromide 

Downstream Products

• 28387-13-5 1,2-bis(benzyloxy)-4-nitrobenzene 
• 57005-09-1 (3,4-Bis-benzyloxy-phenyl)-thiourea 
• 18002-45-4 acetic acid-(3,4-bis-benzyloxy-anilide) 
• 190018-31-6 4-Benzyloxy-3-phenoxy-phenylamine 
• 190018-32-7 4-Benzyloxy-3-phenethyloxy-phenylamine 
• 190018-33-8 4-Benzyloxy-3-cyclopentyloxy-phenylamine 
• 749791-90-0 1-(3,4-Bis-benzyloxy-phenyl)-2-methyl-isothiourea 
• 3635-09-4 2-tosyloxymethyl-6-nitro-1,4-benzodioxane 

Relevant academic research and scientific papers

Preparation and unequivocal identification of the regioisomers of nitrocatechol monobenzyl ether

The four positional isomers of nitrocatechol monobenzyl ether were prepared as intermediates to nitrobenzodioxanes directly from 2-benzyloxyphenol or, through two-four steps, from catechol. These preparations addressed the issue of the certain identificat

New non peptidic C5a receptor antagonists

A series of phenylguanidines which bind to the C5a receptor has been developed. The lead compound 1 (IC50 = 30 μM), discovered through random screening, has been modified to provide 32 (RPR121154) with submicromolar activity. This compound was

Regioselective cleavage reaction of the aromatic methylenedioxy ring. V. Cleavage with sodium alkoxides-alcohols, potassium tert-butoxide-alcohols, dimsyl anion-methyl alcohol, metallic sodium-alcohols, and sodium cyanide in dipolra aprotic solvents

The reaction of aromatic methylenedioxy compounds containing electron-withdrawing groups with dimsyl anion-methyl alcohol, potassium tert-butoxide-alcohols, and metallic sodium-alcohols in dimethyl sulfoxide (DMSO), and with sodium alkoxides-alcohols in hexamethylphosphoramide, gave 3- and 4-hydroxybenzene derivatives in good yield by regioselective attack of the alkoxide ions on the methylenedioxy ring. The formation mechanism of alkoxide ions and the effect of DMSO in the cleavage reaction of the methylenedioxy ring are discussed on the basis of proton nuclear magnetic resonance (1H-NMR) spectra. The reactions of aromatic methylenedioxy compounds (3 and 22) with sodium cyanide in dipolar aprotic solvents gave 4-cyano-3-hydroxybenzene derivatives (23 and 24) by regioselective attack of the cyanide ion on the methylenedioxy ring. The reactions of aromatic methylenedioxy compounds (28-30) containing no electron-withdrawing group with MeONa-MeOH in dipolar aprotic solvents gave non-regioselective cleavage products (31 and 34).

Cleavage of the Methylenedioxy Ring. III. Cleavage with Sodium Benzyloxide in Dimethyl Sulfoxide

Cleavage of the methylenedioxy ring in aromatic formyl (1-3), nitro (4 and 5), and acetyl (30) compounds with N-sodium benzyloxide-benzyl alcohol in dimethyl sulfoxide gave 3-hydroxybenzene derivatives (19, 22-24, 26, 27, and 33).In the case of the acetyl compound 30, the 4-hydroxybenzene derivative (34) was also obtained as a minor product.Regioselective cleavage of the ring in aromatic compounds having electronwithdrawing groups with nucleophilic oxide anions is discussed.Cleavage of the ring in 1-5 and 30 with 2 N sodium methoxide in dimethyl sulfoxide-dimethylformamide was found to be useful for the practical preparation of 3-hydroxybenzene derivatives (6-10 and 31).Keywords - Cleavage of methylenedioxy ring; regioselectivity; piperonals; 3,4-methylenedioxy-nitrobenzene; 3,4-methylenedioxy-acetophenone; sodium methoxide; sodium phenoxide; sodium benzyloxide; dimethyl sulfoxide; dimethylformamide