4-prop-2-enoxyphenol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of hydroquinone (33.00 g, 0.30 mol) and potassium carbonate (45.6 g, 0.33 mol) in dry DMF (250 mL) was stirred at 40° C. for minutes. Allyl bromide (5.20 mL, 0.06 mol) was added and the reaction was stirred overnight. The reaction mixture was partitioned between ethyl acetate and 0.2N HCl. The organic layer was washed twice with water, then dried over sodium sulfate. The organic layer was filtered and evaporated to an oil which was chromatographed over silica gel with hexane/ethyl acetate (4:1) to afford 4-allyloxyphenol. The reaction mixture was partitioned between ethyl acetate and 0.2N HCl The organic layer was washed twice with water dried over sodium sulfate The organic layer was filtered evaporated to an oil which was chromatographed over silica gel with hexane/ethyl acetate (4:1)

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of hydroquinone (33.00g, 0.30 mol) and potassium carbonate (45.6 g, 0.33 mol) in dry DMF ( 250 mL) was stirred at 40° C. for 30 minutes. Allyl bromide (5.20 mL, 0.06 mol) was added and the reaction was stirred overnight. The reaction mixture was partitioned between ethyl acetate and 0.2N HCl. The organic layer was washed twice with water, then dried over sodium sulfate. The organic layer was filtered and evaporated to an oil which was chromatographed over silica gel with hexane/ethyl acetate (4:1) to afford 4-allyloxyphenol. The reaction mixture was partitioned between ethyl acetate and 0.2N HCl The organic layer was washed twice with water dried over sodium sulfate The organic layer was filtered evaporated to an oil which was chromatographed over silica gel with hexane/ethyl acetate (4:1)

Conditions: temp:37.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methacrylic anhydride (6.92 g; 0.045 moles) was added dropwise to a chilled solution of purified 4-allyloxyphenol (7.0 g; 0.047 moles), triethylamine (3.55 g; 0.035 moles), 4-dimethylaminopyridine (0.43 g; 0.004 moles), 2-6-di-tert-butyl-4-methylphenol (0.018 g; 0.08 m moles) and toluene (20 ml) in a stirred 100 ml reaction flask fitted with a reflux condenser, magnetic stirrer and thermocouple probe. During the addition the reaction temperature increased to 37° C. The mixture was heated at 110° C. for 1.5 hour, cooled and washed sequentially with equal volumes of saturated sodium bicarbonate, dilute hydrochloric acid and water. The solution was dried over magnesium sulfate and the solvent removed under reduced pressure to yield 4-allyloxyphenyl methacrylate (8.3 g; 90% yield) as a clear yellow liquid. The structure of the monomer was confirmed by proton and infrared spectral analysis and GC analysis indicated a purity of 90%. fitted with a reflux condenser, magnetic stirrer During the addition the reaction temperature The mixture was heated at 110° C. for 1.5 hour cooled washed sequentially with equal volumes of saturated sodium bicarbonate, dilute hydrochloric acid and water The solution was dried over magnesium sulfate the solvent removed under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of hydroquinone (33.00 g, 0.30 mol) and potassium carbonate (45.6 g, 0.33 mol) in dry DMF (250 mL) was stirred at 40° C. for 30 minutes. Allyl bromide (5.20 mL, 0.06 mol) was added and the reaction was stirred overnight. The reaction mixture was partitioned between ethyl acetate and 0.2N HCl. The organic layer was washed twice with water, then dried over sodium sulfate. The organic layer was filtered and evaporated to an oil which was chromatographed over silica gel with hexane/ethyl acetate (4:1) to afford 4-allyloxyphenol. The reaction mixture was partitioned between ethyl acetate and 0.2N HCl The organic layer was washed twice with water dried over sodium sulfate The organic layer was filtered evaporated to an oil which was chromatographed over silica gel with hexane/ethyl acetate (4:1)

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Fluorobenzaldehyde (3.8 mL, 35.1 mmoles) was added to a solution of the product from Example 60A (4.39 g, 29.3 mmoles) and K2CO3 (8.90 g, 64.4 mmoles) in DMF (29.3 mL). The resulting mixture was heated to 100° C. for 2.5 days and then cooled to room temperature. The crude products were diluted with diethyl ether, extracted with sat. NH4Cl, extracted with H2O (2×), washed with brine, dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by flash chromatography on a prepacked Biotage column (hexane→9:1 hexane:ethyl acetate) on silica gel to provide the title compound (3.50 g, 81%) as a clear colorless oil. cooled to room temperature extracted with sat. NH4Cl extracted with H2O (2×) washed with brine dried (Na2SO4) concentrated under reduced pressure The residue was purified by flash chromatography on a prepacked Biotage column (hexane→9:1 hexane:ethyl acetate) on silica gel

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Allyl iodide (8.2 mL, 89 mmoles) was added to a solution of hydroquinone (7.84 g, 71.2 mmoles) and K2CO3 (19.7 g, 142.4 mmoles) in acetone (102 mmoles). The resulting mixture was heated to 40° C. overnight and concentrated under reduced pressure. The crude products were filtered through a pad of silica with 1:1 hexanes:ethyl acetate. The residue was purified by flash chromatography on a prepacked Biotage column (hexane to 1:1 hexane:ethyl acetate) on silica gel to provide the title compound (4.40 g, 41%). concentrated under reduced pressure The crude products were filtered through a pad of silica with 1:1 hexanes The residue was purified by flash chromatography on a prepacked Biotage column (hexane to 1:1 hexane:ethyl acetate) on silica gel

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of hydroquinone (33.00 g, 0.30 mol) and potassium carbonate (45.6 g, 0.33 mol) in dry DMF (250 mL) was stirred at 40° C. for minutes. Allyl bromide (5.20 mL, 0.06 mol) was added and the reaction was stirred overnight. The reaction mixture was partitioned between ethyl acetate and 0.2N HCl. The organic layer was washed twice with water, then dried over sodium sulfate. The organic layer was filtered and evaporated to an oil which was chromatographed over silica gel with hexane/ethyl acetate (4:1) to afford 4-allyloxyphenol. The reaction mixture was partitioned between ethyl acetate and 0.2N HCl The organic layer was washed twice with water dried over sodium sulfate The organic layer was filtered evaporated to an oil which was chromatographed over silica gel with hexane/ethyl acetate (4:1)

Conditions: temp:0.00; pressure:0.00; stir: