2-ethenylphenol

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

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

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of tert-butyl 4-{4-[(hydroxyimino)methyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (3.46 g) and 2-vinylphenol (1.60 g) in ethyl acetate (50 ml) were added, at room temperature, potassium hydrogencarbonate (5.55 g) and N-chlorosuccinimide (1.78 g), and then one drop of water. After stirring at 60° C. overnight, ethyl acetate and water were added to the reaction mixture, which was extracted with ethyl acetate. The organic extracts were dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by chromatography. This gave tert-butyl 4-{4-[5-(2-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (1.70 g) was extracted with ethyl acetate The organic extracts were dried over sodium sulphate concentrated under reduced pressure The residue was purified by chromatography

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

Procedure: 2-ethenyl phenol was synthesized according to the procedure of Corson et al. (J. Org. Chem., 1958, 23, 544) and silated by standard procedures. 2-t-butyldimethylsiloxy styrene (550 mg, 2.03 mmoles) was dissolved in tetrahydrofuran (4.0 mL). Exo-1-methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane-2-ol (690 mg, 4.06 mmoles) and N-bromosuccinimide were added. One drop of perchloric acid (70%) was added. The reaction was stirred for 11/2 hrs after which time a 1M solution of tetrabutylammonium fluoride in THF (2.5 mL) (any fluoride source, such as KF, NaF, CaF2, HF will suffice) was added and the solution was stirred for an hour. The reaction mixture was diluted with diethyl ether and washed with H2O. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated. It was then chromatographed on SiO2 (10-20% Et2O/hexane) to obtain 210 mg of the desired product in about 95% purity. was added washed with H2O The organic layer was dried over anhydrous Na2SO4 filtered concentrated It was then chromatographed on SiO2 (10-20% Et2O/hexane)

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

Procedure: 2-ethenyl phenol was synthesized according to the procedure of Corson et al. (J. Org. Chem., 1958, 23, 544) and silated by standard procedures. 2-t-butyldimethylsiloxy styrene (550 mg, 2.03 mmoles) was dissolved in tetrahydrofuran (4.0 mL). Exo-1-methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane-2-ol (690 mg, 4.06 mmoles) and N-bromosuccinimide were added. One drop of perchloric acid (70%) was added. The reaction was stirred for 11/2 hrs after which time a 1M solution of tetrabutylammonium fluoride in THF (2.5 mL) (any fluoride source, such as KF, NaF, CaF2, HF will suffice) was added and the solution was stirred for an hour. The reaction mixture was diluted with diethyl ether and washed with H2O. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated. It was then chromatographed on SiO2 (10-20% Et2O/hexane) to obtain 210 mg of the desired product in about 95% purity. was added washed with H2O The organic layer was dried over anhydrous Na2SO4 filtered concentrated It was then chromatographed on SiO2 (10-20% Et2O/hexane)

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

Procedure: The procedure of Example 6 was repeated except that no methanol was added to the starting crude vinylphenol and the alkali aqueous solution. A toluene solution of p-vinylphenol having the same purity (99.1 wt%) as in Example 6 was obtained as a product. However, for 60 hours after the extraction operation a large amount of scale deposited on the inner wall of the extraction tower and line 8, and, as a result, it was impossible to further continue the operation.

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

Procedure: The procedure of Example 6 was repeated except that no methanol was added to the starting crude vinylphenol and the alkali aqueous solution. A toluene solution of p-vinylphenol having the same purity (99.1 wt%) as in Example 6 was obtained as a product. However, for 60 hours after the extraction operation a large amount of scale deposited on the inner wall of the extraction tower and line 8, and, as a result, it was impossible to further continue the operation.

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

Procedure: As a result, 3.5 liters of a toluene solution containing 1.5 mols of a vinylphenol mixture of 37.0 mol% o-vinylphenol, 24.7 mol% m-vinylphenol, 36.9 mol% p-vinylphenol and 1.4 mol% ethylphenol was obtained as the extract. As the raffinate, 10.4 liters of a toluene solution containing 2.6 mols of an ethylphenol mixture of 9.9 mol% o-ethylphenol, 4.0 mol% m-ethylphenol, 85.1 mol% p-ethylphenol and 1.0 mol% vinylphenol was obtained.

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

Procedure: As a result, 3.5 liters of a toluene solution containing 1.5 mols of a vinylphenol mixture of 37.0 mol% o-vinylphenol, 24.7 mol% m-vinylphenol, 36.9 mol% p-vinylphenol and 1.4 mol% ethylphenol was obtained as the extract. As the raffinate, 10.4 liters of a toluene solution containing 2.6 mols of an ethylphenol mixture of 9.9 mol% o-ethylphenol, 4.0 mol% m-ethylphenol, 85.1 mol% p-ethylphenol and 1.0 mol% vinylphenol was obtained.

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

Procedure: The process according to claim 1, wherein said vinylphenol-containing polymerization raw material comprises vinylphenol, non-polymerizable phenols and water, and is a crude reaction product or a partially purified reaction product obtained by dehydrogenation of ethylphenol. containing polymerization raw material reaction product a partially purified reaction product

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of tert-butyl 4-{4-[(hydroxyimino)methyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (3.46 g) and 2-vinylphenol (1.60 g) in ethyl acetate (50 ml) were added, at room temperature, potassium hydrogencarbonate (5.55 g) and N-chlorosuccinimide (1.78 g), and then one drop of water. After stirring at 60° C. overnight, ethyl acetate and water were added to the reaction mixture, which was extracted with ethyl acetate. The organic extracts were dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by chromatography. This gave tert-butyl 4-{4-[5-(2-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (1.70 g) was extracted with ethyl acetate The organic extracts were dried over sodium sulphate concentrated under reduced pressure The residue was purified by chromatography

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of tert-butyl 4-{4-[(hydroxyimino)methyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (3.46 g) and 2-vinylphenol (1.60 g) in ethyl acetate (50 ml) were added, at room temperature, potassium hydrogencarbonate (5.55 g) and N-chlorosuccinimide (1.78 g), and then one drop of water. After stirring at 60° C. overnight, ethyl acetate and water were added to the reaction mixture, which was extracted with ethyl acetate. The organic extracts were dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by chromatography. This gave tert-butyl 4-{4-[5-(2-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (1.70 g) was extracted with ethyl acetate The organic extracts were dried over sodium sulphate concentrated under reduced pressure The residue was purified by chromatography