120125-63-5

Upstream product

• 105-39-5 chloroacetic acid ethyl ester 
• 586-37-8 1-(3-Methoxyphenyl)ethanone 
• 121-71-1 3-Hydroxyacetophenone 

Downstream Products

• 130788-40-8 2-(3-methoxyphenyl)propanal 
• 135657-28-2 ethyl 2-hydroxy-3-(3-methoxyphenyl)-3-butenoate 
• 130788-33-9 (+)-E-cis-2(R),4(R)-4-(3-methoxyphenyl)-2,4-dimethylcyclohexanone oxime 
• 135684-72-9 (+)-cis-5(R),7(R)-hexahydro-5-(3-methoxyphenyl)-5,7-dimethyl-2H-azepine-2-one 
• 130788-29-3 ((S)-2-Methoxymethyl-pyrrolidin-1-yl)-[(R)-4-(3-methoxy-phenyl)-2,4-dimethyl-cyclohex-(Z)-ylidene]-amine 
• 130788-41-9 3'-methoxy-1-methyl-2,3-dihydro-[1,1'-biphenyl]-4(1H)-one 
• 130788-39-5 2-hydroxy-3-(3-methoxyphenyl)-3-butenoic acid 
• 130788-32-8 (+)-trans-2(R),4(S)-4-(3-methoxyphenyl)-2,4-dimethylcyclohexanone 
• 130855-86-6 (+)-cis-2(R),4(R)-4-(3-methoxyphenyl)-2,4-dimethylcyclohexanone 
• 130788-35-1 (+)-5(S),7(R)-5-(3-methoxyphenyl)-5-methyl-7-(N-methyltrifluoroacetamido)octan-2-one 
• 130788-31-7 2(S)-2-methoxymethyl-N-<4'-(3-methoxyphenyl)-4'-methylcyclohexylidene>-1-pyrrolidinamine 
• 135657-30-6 (-)-trans-5(S),7(R)-hexahydro-5-(3-methoxyphenyl)-1,5,7-trimethyl-2-azepinone 
• 130788-34-0 (-)-trans-5(S),7(R)-hexahydro-5-(3-methoxyphenyl)-5,7-dimethyl-2H-azepine-2-one 
• 130788-33-9 (+)-E-trans-2(R),4(S)-4-(3-methoxyphenyl)-2,4-dimethylcyclohexanone oxime 

Relevant academic research and scientific papers

HClO4·SiO2-mediated improved isomerization of glycidic esters to α-hydroxy-β,γ -unsaturated esters: Application in the formal synthesis of (R)-Baclofen and β-phenyl GABA analogues

An efficient isomerization of glycidic esters to corresponding allylic alcohols, viz. α-hydroxy-β,γ -unsaturated esters has been brought about using HClO4·SiO2. Five of these allylic alcohols underwent selective SN2' nucleophilic substitution to generate γ-azido-α,β-unsaturated esters which were readily converted to an antispastic drug Baclofen and four other β-phenyl GABA analogues.

Chiral synthesis of 6,7-benzomorphans: Synthesis of ( -)1(S),2(S),4(R),6(R)-1,2,3,4,5,6-hexahydro-2,6-methano-8-methoxy -1,3,4,6-tetramethyl-3-benzazocine through the chromium hexacarbonyl mediated cyclisation of 1(S),1 ′(R)-1,2-dihydro-7-methoxy-1,4-dimethyl -1 (N-methy-N-trifluoroacetamido-1′-methylethan-2′-yl)naphthalene

(-)1(S),2(S),4(R),6(R)-1,2,3,4,5,6-Hexahydro-2,6-methano-8-methoxy- 1,3,4,6-tetramethyl-3-benzazocine has been synthesised in 86 % enandomeric excess from the α-(v6-chromium tricarbonyl) complex of 1 (S), 1′(R)-1,2-dihydro-7-methoxy-1,4-dimethyl-1-(N-methyl-N-trifluoroacetamido- 1′-methylethan-2/-yl)naphthalene. A precursor of this compound is 2(R),4(,S)-4-(3-methoxyphenyl)-2,4-dimethylcyclohexanone which was obtained through an Enders' type C-methylation reaction of 4-(3-methoxyphenyl)4-methylcyclohexanone using SAMP as the reagent.

A New Synthesis of a Naturally Occuring Isocoumarin. 3,4-Dimethyl-8-hydroxyisocoumarin (Oospolactone)

3,4-Dimethyl-8-methoxyisochroman (5a) on oxidation furnishes 3,4-dimethyl-8-methoxy-3,4-dihydroisocoumarin (6a), and demethylated with hydriodic acid to 3,4-dimethyl-8-hydroxy-3,4-dihydroisocoumarin (7a).Treatment of 6a with N-bromosuccinimide followed by refluxing with triethylamine furnishes 3,4-dimethyl-8-methoxyisocoumarin (8a) which on demethylation with hydriodic acid yields 3,4-dimethyl-8-hydroxyisocoumarin (oospolactone) (9a).Compound 5a and 3,4-dimethyl-6-methoxyisochroman (5b) obtained by treating 3-(m-methoxyphenyl)butan-2-ol (4) with HCHO/HCl are separated by fractional distillation.Compound 4 is obtained from α-(m-methoxyphenyl)propionaldehyde (3) by Grignard reaction with methylmagnesium iodide.The aldehyde (3) is obtained from m-methoxyacetophenone (1) by Darzens glycidic ester condensation followed by hydrolysis and decarboxylation of the resulting product.