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A novel synthesis of isoeugenol, [ring-(U)-(14)C].

Journal of labelled compounds & radiopharmaceuticals (2015-08-27)
John E Immoos
ABSTRACT

A novel method for the preparation of isoeugenol, [ring-(U)-(14)C] is presented. Phenols and phenyl esters substituted in the para position with 1-hydroxyethyl or 1-hydroxypropyl acetate esters when treated with 1,8-diazabicyclo[5.4.0]undec-7-ene in dimethylformamide (DMF) eliminate the alkyl carboxylate function to give the unsaturated compound. The reaction fails with unsubstituted or ether substituted phenyl 1-hydroxyacetate esters.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Diethyl ether, contains 1 ppm BHT as inhibitor, anhydrous, ≥99.7%
Sigma-Aldrich
Diethyl ether, ACS reagent, ≥98.0%, contains ≤2% ethanol and ≤10ppm BHT as inhibitor
Sigma-Aldrich
Diethyl ether, ACS reagent, anhydrous, ≥99.0%, contains BHT as inhibitor
Sigma-Aldrich
Diethyl ether, contains BHT as inhibitor, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥99.8%
Sigma-Aldrich
Diethyl ether, puriss., contains ~5 mg/L 2,6-di-tert.-butyl-4-methylphenol as stabilizer, meets analytical specification of Ph. Eur., BP, ≥99.5% (GC)
Sigma-Aldrich
Diethyl ether, reagent grade, ≥98%, contains ≤2% ethanol and ≤10ppm BHT as inhibitor
Sigma-Aldrich
Diethyl ether, anhydrous, ACS reagent, ≥99.0%, contains BHT as inhibitor