Methyl Chloride → 2-(4-Methylbenzoxazolyl)-5-(hydroxylmethyl)-1,4-bis(hexyloxy)benzene

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Reaction Steps

Herein, the detailed synthetic procedure is described to illustrate the features related to the compound preparations, chemical synthesis, and spectroscopic properties. For the first reaction shown in Scheme 1, activated molecular sieves (5 Å) was added to 100 mL MeOH in 500 mL flask. Into this flask were charged 2-amino-m-cresol (2.39 g, 21.7 mmol) and 2,5-bis(hexyloxy)-4-(hydroxymethyl)benzaldehyde (2.54 g, 21.7 mmol). The resulting mixture solution was heated to reflux overnight. The solution was cooled to room temperature, filtered, and solvent was removed using a rotary evaporator. Then solution of DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone) (4.85 g, 21.4 mmol) in 700 mL CH2Cl2 was added to the above residue. After stirring at room temperature for 2 h, the reaction mixture was treated with 400 mL saturated Na2CO3 and methyl chloride to remove the DDQH by-product, then washed with water and brine, and dried over Na2SO4. After evaporation of the solvent, the solid residues were collected and purified on a silica gel column by using an eluant (hexane:CH3COOEt=15:1). After recrystallization from methanol, the product 2-(4-methylbenzoxazolyl)-5-(hydroxylmethyl)-1,4-bis(hexyloxy)benzene was obtained as an off-white solid (7.8 g, 81.8%), which has the following spectral properties. 1H NMR (CDCl3, 300 MHz, δ): 7.58 (s, 1H), 7.39 (d, J=8.4 Hz, 1H), 7.32 (dd, J=8.4 Hz, J=8.1 Hz, 1H), 7.14 (d, J=7.5 Hz, 1H), 7.06 (s, 1H), 4.74 (d, J=6.6 Hz, 2H), 4.07 (tt, J=6.3 Hz, 4H), 2.68 (s, 3H), 1.83 (m, 4H), 1.58 (m, 4H), 1.34 (m, 8H), 0.89 (m, 6H). MS (EI): [M+H+]+=356.3, [M+Na+]+=462.3.

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