Synthesis of 1,1,5,6-Tetramethyl- and 7-Isopropyl-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene

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Title:Synthesis of 1,1,5,6-Tetramethyl- and 7-Isopropyl-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene
Creators:
Mane, Ramchandra Bhimrao
Kadam, Abhijit Jaysingrao
Salunkhe, Rajashree Sandeep
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 64, 3, pp. 527-532
Uncontrolled Keywords:Sesquiterpenoids, Alkylation, Friedel-Crafts reaction, Cyclization, 1,2,3,4-Tetrahydronaphthalenes

Abstract

4-(2,3-Dimethylphenyl)butanoic acid (<strong>4</strong>) was treated with excess of methyllithium to yield 5-(2,3-dimethylphenyl)-2-methylpentan-2-ol (<strong>6</strong>) which was cyclodehydrated using Dowex 50W-X8 resin, trifluoroacetic acid or polyphosphoric acid (PPA) to furnish 1,1,5,6-tetramethyl-1,2,3,4-tetrahydronaphthalene (<strong>1</strong>). The acid <strong>4</strong> was cyclized with PPA to furnish 5,6-dimethyl-3,4-dihydronaphthalen-1(2<i>H</i>)-one (<strong>5</strong>) which was converted into <strong>1</strong> by reaction with dimethylzinc and titanium tetrachloride. 4-(4-Isopropylphenyl)butanoic acid (<strong>7</strong>) on esterification followed by Grignard reaction with methylmagnesium iodide furnished 5-(4-isopropylphenyl)-2-methylpentan-2-ol (<strong>9</strong>), which was cyclodehydrated as above to yield 7-isopropyl-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene (<strong>2</strong>). <p>

Title:Synthesis of 1,1,5,6-Tetramethyl- and 7-Isopropyl-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene
Creators:
Mane, Ramchandra Bhimrao
Kadam, Abhijit Jaysingrao
Salunkhe, Rajashree Sandeep
Uncontrolled Keywords:Sesquiterpenoids, Alkylation, Friedel-Crafts reaction, Cyclization, 1,2,3,4-Tetrahydronaphthalenes
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:64
Number:3
Page Range:pp. 527-532
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19990527UNSPECIFIED
ID Code:1494
Item Type:Article
Deposited On:06 Feb 2009 17:10
Last Modified:06 Feb 2009 16:10

Citation

Mane, Ramchandra Bhimrao; Kadam, Abhijit Jaysingrao; Salunkhe, Rajashree Sandeep (1999) Synthesis of 1,1,5,6-Tetramethyl- and 7-Isopropyl-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene. Collection of Czechoslovak Chemical Communications, 64 (3). pp. 527-532. ISSN 0010-0765

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