Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
tert-Butylation of 1-Naphthol with tert-Butyl Alcohol or tert-Butyl Chloride in the Presence of Sulfuric Acid or Zinc Chloride
Toshiyuki MIYATATakahiro HAMADATsuneaki HIRASHIMAOsamu MANABEHachiro HIYAMA
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1973 Volume 31 Issue 10 Pages 831-834

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Abstract
tert-Butylation of 1-naphthol with tert-butyl alcohol in acetic acid in the presence of sulfuric acid, and with tert-butyl chloride in tetrachloroethane or chloroform in the presence of anhydrous zinc chloride were studied.
The reaction products were separated and identified.
In the former reaction, the following products were obtained ; 2-tert-butyl-1- naphthol (the main product), 2, 4-di-tert-butyl-1-naphthol, 4-tert-butyl-l-naphthol, 2-tert-butyl-1, 4-naphthoquinone and 3, 3'-di-tert-butyl-4, 4'-dinaphthoquinone.
In the latter, the main product was 3, 6-di-tert-butyl-1-naphthol, and the products described above were also detected.
3, 6-Di-tert-butyl-1-naphthol was obtained in about 40% yield in chloroform, and 4-tert-butyl-l-naphthol was obtained in about 42% yield in tetrachloroethane.
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© The Society of Syhthetic Organic Chemistry, Japan
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