An optimized method for synthesis and purification of 1,1,6-trimethyl-1,2-dihydronaphthalene (TDN)

Alexey Dobrydnev; Andrii Tarasov; Nikolaus Müller; Yulian Volovenko; Doris Rauhut; Rainer Jung

doi:10.1016/j.mex.2019.12.009

An optimized method for synthesis and purification of 1,1,6-trimethyl-1,2-dihydronaphthalene (TDN)

MethodsX. 2019 Dec 16:7:56-61. doi: 10.1016/j.mex.2019.12.009. eCollection 2020.

Authors

Alexey Dobrydnev¹, Andrii Tarasov², Nikolaus Müller³, Yulian Volovenko¹, Doris Rauhut⁴, Rainer Jung²

Affiliations

¹ Department of Organic Chemistry, Faculty of Chemistry, Taras Shevchenko National University of Kyiv, Lva Tolstoho Str. 12, 01033 Kyiv, Ukraine.
² Department of Enology, Hochschule Geisenheim University, Von-Lade-Straße 1, 65366 Geisenheim, Germany.
³ Silvanerweg 9, 55595 Wallhausen, Germany.
⁴ Department of Microbiology and Biochemistry, Hochschule Geisenheim University, Von-Lade-Straße 1, 65366 Geisenheim, Germany.

Abstract

1,1,6-Trimethyl-1,2-dihydronaphthalene (TDN), an aroma compound present in wine, is used for sensory and physicochemical analyses. Therefore, synthesis of TDN of high purity is required for these purposes. Optimization of TDN synthesis in order to facilitate its subsequent purification was described. As a result, ≥99.5 % of TDN purity was reached. •The possibility of using both α-ionone and β-ionone as starting substances was demonstrated•Modifications of the use of reagents in the second and third steps of TDN synthesis were proposed.

Keywords: Enology; High purity; Synthesis and purification of 1,1,6-trimethyl-1,2-dihydronaphthalene (TDN); TDN; Wine.