1570-27-0

Basic information

• Product Name: 8-Hydroxy-3,4-dimethyl-1H-2-benzopyran-1-one
• Synonyms: 8-Hydroxy-3,4-dimethyl-1H-2-benzopyran-1-one;8-Hydroxy-3,4-dimethylisocoumarin;Oospolactone
• CAS NO: 1570-27-0
• Molecular Formula: C11H10 O3
• Molecular Weight: 190.1953
• Mol File: 1570-27-0.mol

Chemical Properties

• Boiling Point: 346.5°Cat760mmHg
• Flash Point: 153.9°C
• Appearance: /
• Density: 1.255g/cm³
• Vapor Pressure: 2.86E-05mmHg at 25°C
• Refractive Index: 1.589
• CAS DataBase Reference: 8-Hydroxy-3,4-dimethyl-1H-2-benzopyran-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Hydroxy-3,4-dimethyl-1H-2-benzopyran-1-one(1570-27-0)
• EPA Substance Registry System: 8-Hydroxy-3,4-dimethyl-1H-2-benzopyran-1-one(1570-27-0)

Safety Data

• Hazardous Substances Data: 1570-27-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H10O3/c1-6-7(2)14-11(13)10-8(6)4-3-5-9(10)12/h3-5,12H,1-2H3

Upstream product

• 6125-50-4 2-(2'-carboxy-3'-methoxyphenyl)propanoic acid 
• 586-37-8 1-(3-Methoxyphenyl)ethanone 
• 120125-65-7 3,4-dimethyl-8-methoxyisochroman 
• 120125-64-6 3-(m-methoxyphenyl)butan-2-ol 
• 130788-40-8 2-(3-methoxyphenyl)propanal 
• 120125-63-5 cis/trans-ethyl 2-(3-methoxyphenyl)-2-methyl-1-oxirane-1-carboxylate 
• 121-71-1 3-Hydroxyacetophenone 
• 1025812-82-1 2,2-ethylenedioxy-3-(3'-methoxymethoxyphenyl)butane 
• 127972-99-0 1-(3-bromophenoxy)-1-ethoxyethane 
• 51038-67-6 3-(3'-hydroxyphenyl)-2-butanone 
• 591-20-8 3-Bromophenol 
• 1026727-13-8 3,4-dihydro-8-hydroxy-3-methoxy-3,4-dimethylisocoumarin 
• 6125-52-6 3,4-dimethyl-8-methoxyisocoumarin 
• 120125-66-8 3,4-dimethyl-8-methoxy-3,4-dihydroisocoumarin 

Relevant articles and documents

8-HYDROXY-SUBSTITUTED ISOCOUMARINS BY LITHIATION OF BENZENE DERIVATIVES PROMOTED BY β-FUNCTIONALISED ALKYL GROUPS. A REGIOSELECTIVE AND SIMPLE SYNTHESIS OF OOSPOLACTONE

3-(3-hydroxyphenyl)-2-butanone (obtained in 3 steps from 3-bromophenol and 3-chloro-2-butanone) was ketalised with ethylene glycol and protected at the phenolic OH as the methoxymethyl ether.The intermediate diacetal thus obtained underwent hydrogen-metal exchange with n-butyllithium; the metallated intermediate, after carbonation, methanolysis of acetal groups and elimination of methanol, regioselectively afforded the title compound (8-hydroxy-3,4-dimethylisocoumarin).

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.

A New Synthesis of Tetrahydrocapillarine, O-Methylglomelline and Oospolactone

Pyridine catalysed acylation of a number of homophthalic acids with various acid anhydrides has been extensively studied, leading to the synthesis of several substituted isocoumarins including the natural products mentioned above.