Highly regioselective one-pot synthesis of 7-hydroxy-6-methylphthalide from 3-hydroxy-4-methylbenzylalcohol

Meili Duan, Michael D. Toney

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

7-Hydroxy-6-methylphthalide 2 was synthesized with high regioselectivity and moderate yield using a novel one-pot synthesis that employed 3-hydroxy-4-methylbenzylalcohol 1 and formaldehyde in the presence of tin(IV) chloride as catalyst and triethylamine as base. The proposed mechanism of the formation of 2 involves ortho-formylation followed by hemiacetal formation and oxidation.

Original languageEnglish (US)
Pages (from-to)2869-2874
Number of pages6
JournalSynthetic Communications
Volume35
Issue number22
DOIs
StatePublished - 2005

Fingerprint

Regioselectivity
Tin
Formaldehyde
Chlorides
Oxidation
Catalysts
triethylamine

Keywords

  • 3-Hydroxy-4-methylbenzylalcohol
  • 7-hydroxy-6-methylphthalide
  • One-pot synthesis
  • Regioselective

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Highly regioselective one-pot synthesis of 7-hydroxy-6-methylphthalide from 3-hydroxy-4-methylbenzylalcohol. / Duan, Meili; Toney, Michael D.

In: Synthetic Communications, Vol. 35, No. 22, 2005, p. 2869-2874.

Research output: Contribution to journalArticle

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