4-prop-2-enylphenol

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

Procedure: To a solution of 2.142 g (15.96 mmol) of 4-(2-propenyl)phenol (prepared as in Example 1) in 15 mL of methylene chloride was added 2.351 g (22.19 mmol) of cyanogen bromide (Aldrich). The mixture was cooled in an ice-salt bath and 3 mL (22 mmol) of triethylamine was added dropwise with stirring. The mixture was stirred for an additional 15 minutes. The solvent was removed under vacuum and the mixture was transferred to a separatory funnel with 25 mL of water and 75 mL of petroleum ether (30-60° C. boiling range). The aqueous and organic layers were separated. The organic layer was washed with three 50 mL portions 6 N hydrochloric and one 50 mL portion of saturated sodium bicarbonate, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under vacuum to yield 1.668 g (66%) of crude 1-cyanato-4-(2-propenyl)benzene. The product was distilled to yield 1.307 g (51%) of 1-cyanato-4-(2-propenyl)benzene. The structure of the product was verified by IR and NMR spectroscopy. The product can be further purified by passing the product through a silica gel column using 1% toluene in petroleum ether as the solvent system. The mixture was cooled in an ice-salt bath The mixture was stirred for an additional 15 minutes The solvent was removed under vacuum the mixture was transferred to a separatory funnel with 25 mL of water and 75 mL of petroleum ether (30-60° C. boiling range) The aqueous and organic layers were separated The organic layer was washed with three 50 mL portions 6 N hydrochloric one 50 mL portion of saturated sodium bicarbonate, dried over anhydrous magnesium sulfate filtered The solvent was removed under vacuum

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

Procedure: To 50.01 g (337.4 mmol) of 1-methoxy-4-(2-propenyl)benzene (Aldrich Chemical Company, Milwaukee, Wis.) dissolved in 300 mL of anhydrous methylene chloride was added dropwise 375 mL (375 mmol) of 1.0 M boron tribromide (Aldrich) in methylene chloride. The reaction was run under nitrogen at room temperature and the mixture was stirred for 1 hour. The mixture was poured over 1000 mL of crushed ice, stirred for 5 minutes, and transferred to a separatory funnel. The organic layer was drained and saved. The boron salts were transferred to a filter containing Celite™ (Aldrich Chemical Co., Milwaukee, Wis.) and the filter containing the salts was washed with portions of methylene chloride and then water. The filtrate was transferred to a separatory funnel and the organic and aqueous layers were separated. The aqueous layer was extracted with four 100mL portions of methylene chloride. The methylene chloride solutions were pooled, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under vacuum to yield 25.27 g (56%) of crude 4-(2-propenyl)phenol. The crude product was distilled twice at reduced pressure to yield 20.34 g (45%) of 4-(2-propenyl)phenol. The NMR data was consistent with that reported by Rajashekhar and coworkers (J. Biol. Chem. 1984, 259, 6925). was run under nitrogen at room temperature stirred for 5 minutes transferred to a separatory funnel containing Celite™ (Aldrich Chemical Co., Milwaukee, Wis.) the filter containing the salts was washed with portions of methylene chloride The filtrate was transferred to a separatory funnel the organic and aqueous layers were separated The aqueous layer was extracted with four 100mL portions of methylene chloride dried over anhydrous magnesium sulfate filtered The solvent was removed under vacuum

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

Procedure: 4-Allylphenol, (6.14 g, 0.046 moles), 4-methoxybenzyl chloride, (6.3 ml, 0.046 moles), potassium carbonate (8.3 g, 0.06 moles) and a catalytic amount of potassium iodide were mixed together in about 200 ml acetone, and heated to reflux, with stirring. The reaction was allowed to proceed overnight, then cooled to room temperature and diluted with about 100 ml water. The product was extracted into ethyl acetate (3 times, 300 ml each time), and then dried over magnesium sulfate/potassium carbonate, filtered and concentrated in vacuo to yield the title compound as a light yellow solid, m.p. 59°-61° C. heated to reflux The product was extracted into ethyl acetate (3 times, 300 ml each time) dried over magnesium sulfate/potassium carbonate filtered concentrated in vacuo

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

Procedure: 4-Allylphenol, (6.14 g, 0.046 moles), 4-methoxybenzyl chloride, (6.3 ml, 0.046 moles), potassium carbonate (8.3 g, 0.06 moles) and a catalytic amount of potassium iodide were mixed together in about 200 ml acetone, and heated to reflux, with stirring. The reaction was allowed to proceed overnight, then cooled to room temperature and diluted with about 100 ml water. The product was extracted into ethyl acetate (3 times, 300 ml each time), and then dried over magnesium sulfate/potassium carbonate, filtered and concentrated in vacuo to yield the title compound as a light yellow solid, m.p. 59-61° C. heated to reflux The product was extracted into ethyl acetate (3 times, 300 ml each time) dried over magnesium sulfate/potassium carbonate filtered concentrated in vacuo

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

Procedure: To a solution of 2.142 g (15.96 mmol) of 4-(2-propenyl)phenol (prepared as in Example 1) in 15 mL of methylene chloride was added 2.351 g (22.19 mmol) of cyanogen bromide (Aldrich). The mixture was cooled in an ice-salt bath and 3 mL (22 mmol) of triethylamine was added dropwise with stirring. The mixture was stirred for an additional 15 minutes. The solvent was removed under vacuum and the mixture was transferred to a separatory funnel with 25 mL of water and 75 mL of petroleum ether (30-60° C. boiling range). The aqueous and organic layers were separated. The organic layer was washed with three 50 mL portions 6 N hydrochloric and one 50 mL portion of saturated sodium bicarbonate, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under vacuum to yield 1.668 g (66%) of crude 1-cyanato-4-(2-propenyl)benzene. The product was distilled to yield 1.307 g (51%) of 1-cyanato-4-(2-propenyl)benzene. The structure of the product was verified by IR and NMR spectroscopy. The product can be further purified by passing the product through a silica gel column using 1% toluene in petroleum ether as the solvent system. The mixture was cooled in an ice-salt bath The mixture was stirred for an additional 15 minutes The solvent was removed under vacuum the mixture was transferred to a separatory funnel with 25 mL of water and 75 mL of petroleum ether (30-60° C. boiling range) The aqueous and organic layers were separated The organic layer was washed with three 50 mL portions 6 N hydrochloric one 50 mL portion of saturated sodium bicarbonate, dried over anhydrous magnesium sulfate filtered The solvent was removed under vacuum

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

Procedure: To a solution of 2.142 g (15.96 mmol) of 4-(2-propenyl)phenol (prepared as in Example 1) in 15 mL of methylene chloride was added 2.351 g (22.19 mmol) of cyanogen bromide (Aldrich). The mixture was cooled in an ice-salt bath and 3 mL (22 mmol) of triethylamine was added dropwise with stirring. The mixture was stirred for an additional 15 minutes. The solvent was removed under vacuum and the mixture was transferred to a separatory funnel with 25 mL of water and 75 mL of petroleum ether (30-60° C. boiling range). The aqueous and organic layers were separated. The organic layer was washed with three 50 mL portions 6 N hydrochloric and one 50 mL portion of saturated sodium bicarbonate, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under vacuum to yield 1.668 g (66%) of crude 1-cyanato-4-(2-propenyl)benzene. The product was distilled to yield 1.307 g (51%) of 1-cyanato-4-(2-propenyl)benzene. The structure of the product was verified by IR and NMR spectroscopy. The product can be further purified by passing the product through a silica gel column using 1% toluene in petroleum ether as the solvent system. The mixture was cooled in an ice-salt bath The mixture was stirred for an additional 15 minutes The solvent was removed under vacuum the mixture was transferred to a separatory funnel with 25 mL of water and 75 mL of petroleum ether (30-60° C. boiling range) The aqueous and organic layers were separated The organic layer was washed with three 50 mL portions 6 N hydrochloric one 50 mL portion of saturated sodium bicarbonate, dried over anhydrous magnesium sulfate filtered The solvent was removed under vacuum

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

Procedure: To 50.01 g (337.4 mmol) of 1-methoxy-4-(2-propenyl)benzene (Aldrich Chemical Company, Milwaukee, Wis.) dissolved in 300 mL of anhydrous methylene chloride was added dropwise 375 mL (375 mmol) of 1.0 M boron tribromide (Aldrich) in methylene chloride. The reaction was run under nitrogen at room temperature and the mixture was stirred for 1 hour. The mixture was poured over 1000 mL of crushed ice, stirred for 5 minutes, and transferred to a separatory funnel. The organic layer was drained and saved. The boron salts were transferred to a filter containing Celite™ (Aldrich Chemical Co., Milwaukee, Wis.) and the filter containing the salts was washed with portions of methylene chloride and then water. The filtrate was transferred to a separatory funnel and the organic and aqueous layers were separated. The aqueous layer was extracted with four 100mL portions of methylene chloride. The methylene chloride solutions were pooled, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under vacuum to yield 25.27 g (56%) of crude 4-(2-propenyl)phenol. The crude product was distilled twice at reduced pressure to yield 20.34 g (45%) of 4-(2-propenyl)phenol. The NMR data was consistent with that reported by Rajashekhar and coworkers (J. Biol. Chem. 1984, 259, 6925). was run under nitrogen at room temperature stirred for 5 minutes transferred to a separatory funnel containing Celite™ (Aldrich Chemical Co., Milwaukee, Wis.) the filter containing the salts was washed with portions of methylene chloride The filtrate was transferred to a separatory funnel the organic and aqueous layers were separated The aqueous layer was extracted with four 100mL portions of methylene chloride dried over anhydrous magnesium sulfate filtered The solvent was removed under vacuum

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

Procedure: To 50.01 g (337.4 mmol) of 1-methoxy-4-(2-propenyl)benzene (Aldrich Chemical Company, Milwaukee, Wis.) dissolved in 300 mL of anhydrous methylene chloride was added dropwise 375 mL (375 mmol) of 1.0 M boron tribromide (Aldrich) in methylene chloride. The reaction was run under nitrogen at room temperature and the mixture was stirred for 1 hour. The mixture was poured over 1000 mL of crushed ice, stirred for 5 minutes, and transferred to a separatory funnel. The organic layer was drained and saved. The boron salts were transferred to a filter containing Celite™ (Aldrich Chemical Co., Milwaukee, Wis.) and the filter containing the salts was washed with portions of methylene chloride and then water. The filtrate was transferred to a separatory funnel and the organic and aqueous layers were separated. The aqueous layer was extracted with four 100mL portions of methylene chloride. The methylene chloride solutions were pooled, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under vacuum to yield 25.27 g (56%) of crude 4-(2-propenyl)phenol. The crude product was distilled twice at reduced pressure to yield 20.34 g (45%) of 4-(2-propenyl)phenol. The NMR data was consistent with that reported by Rajashekhar and coworkers (J. Biol. Chem. 1984, 259, 6925). was run under nitrogen at room temperature stirred for 5 minutes transferred to a separatory funnel containing Celite™ (Aldrich Chemical Co., Milwaukee, Wis.) the filter containing the salts was washed with portions of methylene chloride The filtrate was transferred to a separatory funnel the organic and aqueous layers were separated The aqueous layer was extracted with four 100mL portions of methylene chloride dried over anhydrous magnesium sulfate filtered The solvent was removed under vacuum

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

Procedure: Polymerization was carried out in the same manner as in Example 18 except that 4,4'-biphenol and eugenol were replaced by the following bisphenol (BP-16) (21.9 g) ##STR110## and 4-allylphenol (1.6 g), to obtain a polycarbonate comprising the following repeating units and end groups in the following copolymerization ratios wherein bisphenol A, BP-16 and 4-allylphenol structures were present in a molar ratio of 82:15:3. ##STR111## Polymerization

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

Procedure: To a -78° C. cold solution of 4-allylanisol (14.6 ml, 95 mmol) in CH2Cl2 (300 ml) BBr3 (100 ml, 0.1 mol, 1 mol/l in CH2Cl2) was added dropwise. The reaction mixture was then allowed to warm up to room temperature. After 1 hour, the reaction mixture was cooled to 0° C. and quenched slowly with H2O (90 ml). The resulting aqueous phase was extracted with CH2Cl2 (2×100 ml). The combined organic phases were dried over Na2SO4 and concentrated. The residue was chromatographed over silica gel (hexane-ethyl acetate 9:1) to provide 4-allylphenol (11.3 g, 89%) as a purple oil, MS: m/e=134 (M+). the reaction mixture was cooled to 0° C. quenched slowly with H2O (90 ml) The resulting aqueous phase was extracted with CH2Cl2 (2×100 ml) The combined organic phases were dried over Na2SO4 concentrated The residue was chromatographed over silica gel (hexane-ethyl acetate 9:1)

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

Procedure: 4-allylphenol (8.9 g, 66.3 mmol) was dissolved in CH2Cl2 (180 ml). After addition of NaHCO3 (8.4 g, 99.5 mmol), m-chloroperbenzoic acid 70% (18 g, 73 mmol) was added portionwise. After 6 hours at room temperature, additional NaHCO3 (8.4 g, 99.5 mmol) and m-chloroperbenzoic acid 70% (18 g, 73 mmol) were added. After 17 hours, the reaction mixture was washed with sat. NaHCO3 (200 ml) and the resulting aqueous phases were extracted with CH2Cl2 (3×10 ml). The combined organic phases were washed with sat. Na2S2O3 (2×100 ml), dried over Na2SO4 and concentrated. The residue was chromatographed over silica gel (hexan-ethyl acetate 9:1 then 1:1) to provide (RS)-4-oxiranylmethyl-phenol (3.77 g, 38%) as yellow solid, m.p. 54°-57° C. and MS: m/e=150 (M+). was added portionwise After 17 hours the reaction mixture was washed with sat. NaHCO3 (200 ml) the resulting aqueous phases were extracted with CH2Cl2 (3×10 ml) The combined organic phases were washed with sat. Na2S2O3 (2×100 ml) dried over Na2SO4 concentrated The residue was chromatographed over silica gel (hexan-ethyl acetate 9:1

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

Procedure: To a solution of 2.142 g (15.96 mmol) of 4-(2-propenyl)phenol (prepared as in Example 1) in 15 mL of methylene chloride was added 2.351 g (22.19 mmol) of cyanogen bromide (Aldrich). The mixture was cooled in an ice-salt bath and 3 mL (22 mmol) of triethylamine was added dropwise with stirring. The mixture was stirred for an additional 15 minutes. The solvent was removed under vacuum and the mixture was transferred to a separatory funnel with 25 mL of water and 75 mL of petroleum ether (30-60° C. boiling range). The aqueous and organic layers were separated. The organic layer was washed with three 50 mL portions 6N hydrochloric and one 50 mL portion of saturated sodium bicarbonate, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed under vacuum to yield 1.668 g (66%) of crude 1-cyanato-4-(2-propenyl)benzene. The product was distilled to yield 1.307 g (51%) of 1-cyanato-4-(2-propenyl)benzene. The structure of the product was verified by IR and NMR spectroscopy. The product can be further purified by passing the product through a silica gel column using 1% toluene in petroleum ether as the solvent system. The mixture was cooled in an ice-salt bath The mixture was stirred for an additional 15 minutes The solvent was removed under vacuum the mixture was transferred to a separatory funnel with 25 mL of water and 75 mL of petroleum ether (30-60° C. boiling range) The aqueous and organic layers were separated The organic layer was washed with three 50 mL portions 6N hydrochloric one 50 mL portion of saturated sodium bicarbonate, dried over anhydrous magnesium sulfate filtered The solvent was removed under vacuum