Design and synthesis of (E)-4-((3-ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid

Bhaskar C. Das, George W. Kabalka

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

(E)-4-((3-Ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid, 6, was synthesized in 87% starting from β-cyclocitral. The target compound 6 was synthesized starting from 1 via a Grignard reaction to form alcohol 2. Compound 2 was converted to Wittig salt 3 by treatment with aldehyde 4 in butyllithium and hexane at -78 °C to form ester 5. Ester 5 was saponified and, following acidification, acid 6 was isolated as white solid yield 87%.

Original languageEnglish (US)
Pages (from-to)4695-4696
Number of pages2
JournalTetrahedron Letters
Volume49
Issue number32
DOIs
StatePublished - Aug 4 2008

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Benzoic Acid
Esters
Acidification
Hexanes
Aldehydes
Salts
Alcohols
Acids
butyllithium

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Design and synthesis of (E)-4-((3-ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid. / Das, Bhaskar C.; Kabalka, George W.

In: Tetrahedron Letters, Vol. 49, No. 32, 04.08.2008, p. 4695-4696.

Research output: Contribution to journalArticle

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