ChemInform Abstract: A Facile Synthesis of 1,1,6‐Trimethyl‐1,2‐dihydronaphthalene.

Abstract

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

“…The synthesis of TDN ( 1 ) was based on the protocol reported by Miginiac [12] and modified according to our experience in order to obtain analytical specimens of TDN ( 1 ) of high purity. No significant changes were applied to the first step: synthesis of ionene ( 2 ).…”

“…Being impurity with similar physical properties to TDN, 1,2,6-trimethylnaphthalene ( 5 ) was difficult to remove from the obtained TDN ( 1 ). Following the original protocol of Miginiac [12], 1,2,6-trimethylnaphthalene ( 5 ) was formed in the presence of excess of NBS [13] and remained in the final TDN ( 1 ) in a quantity up to 5 % (for its spectral data refer Mayer and Duswalt [14]). As a result, 96 % was the highest purity of TDN specimen reached by Method 1 .…”

“…In order to avoid side reactions caused by an excess of NBS, only half of the stoichiometric amount of NBS was added in Method 2 compared to the original protocol [12]. Thereby, the resulting mixture of unreacted ionene ( 2 ) and bromoionene ( 6 ) was treated with Hünig's base affording approximately an equimolar mixture of ionene ( 2 ) and TDN ( 1 ).…”

“…The optimization of the original method of TDN preparation [12] was described. The modifications imply using reduced amount of N -bromosuccinimide and N , N -diisopropylethylamine instead of N , N -diethylaniline.…”

Effects of sulphur nutrition during potato cultivation on the formation of acrylamide and aroma compounds during cooking

“…1,2-Dihydro-1,1,6-trimethylnaphthalene was prepared by converting a-ionone to ionene, using iodine, and then methylating the ionene using N-bromosuccinimide, benzoyl peroxide and N,N-diethylaniline (Miginiac, 1990). Isobutyltrimethylpyrazine was prepared by reacting isobutyllithium with trimethylpyrazine under nitrogen at 0°C (Rizzi, 1968; warning!…”