Synthesis of 4- 4-vinylbenzyl oxy phenol

The compound was prepared after a shght modification of a previously pubhshed protocol [54]. 1,4-hydroquinone (8.8 g, 80 mmol), 4-vinylbenzyl chloride (3.0 g, 20 mmol), dried, powdered potassium carbonate (2.8 g, 20 mmol) and Ahquat336 (0.8 g, 2 mmol) were dissolved in acetone (75 mL) and the mixture heated to 

80 °C for 24 h. After cooling to room temperature the mixture was concentrated in vacuo, chloroform (30 ml) added and the mixture filtered through Celite. The crude product was purified with flash column chromatography (ethyl acetate/ hexane 9 1, Rf = 0.76, I2 stain) to yield an orange solid (1.66 g, 36 %). 

This compound was prepared after a previously published procedure [55]. The 4-((4-vinylbenzyl)oxy)phenol (1 g, 4.4 mmol) was dissolved in tetrahydrofuran (2 mL) and formaldehyde (37 %, 1 mL) and aqueous sodium hydroxide solution (2.6 M, 2.5 mL) were added. The brown suspension was stirred for two days at room temperature, subsequently hydrochloric acid (0.1 M, 5 mL) were added and the aqueous phase extracted with ethyl acetate (2 x 15 mL). The combined organic layers were dried over sodium sulfate and the solvent removed in vacuo. After purification with column chromatography (hexane/ethyl acetate 1 1, FeCL stain, Rf = 0.3) a pale yellow powder was obtained (372 mg, 59 %). 

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