Synthesis of (+/-)-7,8-and 5,6-dimethyl-2-(2-hydroxyisopropyl) tetralins

Authors
Kadam, AJ Desai, UV Mane, RB
Citation
Aj. Kadam et al., Synthesis of (+/-)-7,8-and 5,6-dimethyl-2-(2-hydroxyisopropyl) tetralins, I J CHEM B, 39(10), 2000, pp. 752-756
Citations number
15
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY
ISSN journal
03764699 → ACNP
Volume
39
Issue
10
Year of publication
2000
Pages
752 - 756
Database
ISI
SICI code
0376-4699(200010)39:10<752:SO(5T>2.0.ZU;2-I
Abstract
7,8-Dimethyl-1-tetralone 4 on sodium borohydride reduction followed by Vils meier-Haack reaction furnishes 7,8-dimethyl-3,4-dihydro-2-naphthaldehyde 10 . Reduction of 10 followed by oxidation with Jones reagent yields 7,8-dimet hyl-1,2,3,4-tetrahydro-2-naphthoic acid 12 which on treatment with excess o f methyllithium affords 7,8-dimethyl-2-(2-hydroxyisopropyl) tetralin 2. 5,6 -dimethyl-1-tetralone 5 is converted into the 5,6-dimethyl-2-(2-hydroxyisop ropyl)tetralin 3 by following similar set of reactions as described above.