A convenient solvent-specific synthesis of 4-[4-acetoxy-3-(3-methylbut-2- enyl)phenyl]butyric acid

Majekodunmi O. Fatope, Joseph I. Okogun

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Abstract

Three types of reaction, esterification, C-alkenylation, and O-alkenylation, have been observed between the di-anion (4) and 1-bromo-3-methylbut-2-ene (5) in different solvent systems. Our studies of the effect of the medium on the behaviour of the di-anion (4) towards electrophilic attack by the bromo-alkene (5) resulted in the synthesis of analogues (2) and (6d) of a known anti-sickling agent (3) in high yield. The regioselectivity of the alkenylation reactions is rationalised in terms of solvent polarity.

Original languageEnglish
Pages (from-to)1601-1603
Number of pages3
JournalJournal of the Chemical Society. Perkin Transactions 1
Publication statusPublished - 1982

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Alkenylation
Butyric Acid
Anions
Regioselectivity
Esterification
Alkenes

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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AB - Three types of reaction, esterification, C-alkenylation, and O-alkenylation, have been observed between the di-anion (4) and 1-bromo-3-methylbut-2-ene (5) in different solvent systems. Our studies of the effect of the medium on the behaviour of the di-anion (4) towards electrophilic attack by the bromo-alkene (5) resulted in the synthesis of analogues (2) and (6d) of a known anti-sickling agent (3) in high yield. The regioselectivity of the alkenylation reactions is rationalised in terms of solvent polarity.

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