9-Anthracenylmethyl methacrylate synthesis

9-Anthracenylmethyl methacrylate (9-AMM)is generally synthesized by reacting 9-Anthracene-methanol with methylene chloride and methacryloyl chloride in the presence of a base triethylamine. 
Experimental procedrure: 9-Anthracene-methanol 9.3g (45mmol), methylene chloride 60ml and methacryloyl chloride 8g (77mmol) were charged into a 300ml three-necked flask equipped with a stirrer and thermometer. Methylene chloride 10ml solution of triethylamine 6.0g (59mmol) was added dropwise while cooling the slurry with ice water. After completion of the dropwise addition, the slurry became a homogeneous solution. Then allowed to stand overnight while cooling in ice water. The hydrochloride salt of triethylamine floating on the liquid surface and water 30ml were sufficiently added. Further stirred to dissolve. Again washed with water 30ml, the obtained methylene chloride solution was dried over anhydrous sodium sulfate. Further methanol was added to the filtered methylene chloride solution 100ml, stored in the refrigerator and recrystallized. After 2 days, the precipitated crystals were suction filtered and dried. Pale yellow microcrystals 7.1g were obtained. Analysis results of the obtained substance are as shown below, this compound was confirmed to be 9-Anthracenylmethyl methacrylate by 1H-NMR, IR. Yield 58mol%. Melting point: 59-60 ° CIR (KBr, cm-1): 1715, 1624, 1450, 1320, 1296, 1164, 1150, 1060, 1008, 964, 946, 892, 740, 700, 640, 600, 568, 500. 1H-NMR (CDCl3, ppm): δ1.92 (s, 3H, methyl), 5.50 (s, 1H, vinyl), 6.05 (s, 1H, vinyl), 6.22 (s, 2H, methylene group), 7.44-7.60 (m, 4H, anthracene ring), 8.03 (d, J = 10Hz, 2H, anthracene ring), 8, 38 (d, J = 10Hz, 2H, anthracene ring), 8.51 (s, 1H, anthracene ring).