ChemicalBook CAS DataBase List 5-Chloro-8-hydroxy-3-methyl-1-oxoisochroman-7-carboxylic acid

5-Chloro-8-hydroxy-3-methyl-1-oxoisochroman-7-carboxylic acid synthesis

13synthesis methods

Product Name:5-Chloro-8-hydroxy-3-methyl-1-oxoisochroman-7-carboxylic acid
CAS Number:19165-63-0
Molecular formula:C11H9ClO5
Molecular Weight:256.64

1123-63-3 Synthesis

1123-63-3
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5-Chloro-8-hydroxy-3-methyl-1-oxoisochroman-7-carboxylic acid

19165-63-0
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Yield:-

Steps:

Multi-step reaction with 6 steps
1.1: potassium carbonate / acetone / 12 h / Reflux
2.1: potassium hydroxide; potassium permanganate / water / 24 h / 80 °C / Reflux
3.1: 2,2,6,6-tetramethylpiperidinyl-lithium / tetrahydrofuran / 4 h / -50 °C
3.2: 1 h / -50 - 20 °C / pH < 1
4.1: boron trichloride / dichloromethane / 2 h / 0 °C / Inert atmosphere
5.1: titanium tetrachloride / dichloromethane / 22 h / -10 - 23 °C / Inert atmosphere
6.1: silver nitrate; dihydrogen peroxide / acetonitrile / 15 h / 50 °C / Reflux

References:

Lenz, Cesar Antonio;Rychlik, Michael [Tetrahedron Letters,2013,vol. 54,# 8,p. 883 - 886]