4-Methylbenzaldehyde → 2-(2-Hydroxy-2-p-methylphenylethyl)-3,5,6-trimethylpyrazine

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Reaction Steps

To a solution of phenyllithium in 150 milliliters 7:3 benzene-ether (0.1 mole) at 0° C. was slowly added a solution of 13.6 grams of tetramethylpyrazine (0.1 mole). The mixture was stirred at room temperature for 2 hours and heated under reflux for 1.5 hours. The mixture was cooled to 0° C., and a solution of 12.0 grams of p-tolualdehyde (0.1 mole) in 50 milliliters of ether was added dropwise. The reaction mixture was stirred at room temperature for 1 hour and then treated in the manner of Example I. The crude product was crystallized from ether to yield 10.7 grams of product (42%) as fine white needles, m.p. 99°-101° C. Analysis Calculated for C16H20N2O: C,74.96; H,7.86; N,10.93 Found: 75.19; 7.96; 10.88

Provenance & Evidence