Cyclohexane, [2-(ethenyloxy)ethyl]-

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

Procedure: Subsequently, 5.78 g of 2-cyclohexylethyl vinyl ether as the vinyl ether compound and 1.45 g of 2% camphorsulfonic acid (PGMEA solution) were added to Solution p-1, and the mixture was stirred at room temperature for 4 hours. After 1.05 g of 6% triethylamine (PGMEA solution) was added and the mixture was stirred for a while, the reaction solution was transferred to a separating funnel containing 165 mL of ethyl acetate, and the organic layer was washed with 200 mL of distilled water three times. The organic layer was concentrated by an evaporator to remove ethyl acetate, and this reaction solution was added dropwise in 2 L of hexane. A part of the obtained precipitate was sampled for NMR measurement, and the remaining was dissolved in 70 g of PGMEA. From the obtained solution, the low boiling point solvent was removed by an evaporator to obtain 105.6 g of a PGMEA solution (32.7 mass %) of Resin (P-1). the mixture was stirred for a while the reaction solution was transferred to a separating funnel the organic layer was washed with 200 mL of distilled water three times The organic layer was concentrated by an evaporator to remove ethyl acetate this reaction solution was added dropwise in 2 L of hexane A part of the obtained precipitate was sampled for NMR measurement the remaining was dissolved in 70 g of PGMEA From the obtained solution, the low boiling point solvent was removed by an evaporator

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

Procedure: Subsequently, 5.78 g of 2-cyclohexylethyl vinyl ether as the vinyl ether compound and 1.45 g of 2% camphorsulfonic acid (PGMEA solution) were added to Solution p-1, and the mixture was stirred at room temperature for 4 hours. After 1.05 g of 6% triethylamine (PGMEA solution) was added and the mixture was stirred for a while, the reaction solution was transferred to a separating funnel containing 165 mL of ethyl acetate, and the organic layer was washed with 200 mL of distilled water three times. The organic layer was concentrated by an evaporator to remove ethyl acetate, and this reaction solution was added dropwise in 2 L of hexane. A part of the obtained precipitate was sampled for NMR measurement, and the remaining was dissolved in 70 g of PGMEA. From the obtained solution, the low boiling point solvent was removed by an evaporator to obtain 105.6 g of a PGMEA solution (32.7 mass %) of Resin (P-1). the mixture was stirred for a while the reaction solution was transferred to a separating funnel the organic layer was washed with 200 mL of distilled water three times The organic layer was concentrated by an evaporator to remove ethyl acetate this reaction solution was added dropwise in 2 L of hexane A part of the obtained precipitate was sampled for NMR measurement the remaining was dissolved in 70 g of PGMEA From the obtained solution, the low boiling point solvent was removed by an evaporator

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

Procedure: Cyclohexylethyl alcohol was mixed with ethyl vinyl ether. Mercury acetate was added thereto and this mixture was stirred at room temperature for 12 hours. The resultant reaction mixture was extracted with ethyl acetate and water, and the extract was washed with water and then distilled under reduced pressure to obtain cyclohexylethyl vinyl ether (X-1) as the target compound. The resultant reaction mixture was extracted with ethyl acetate and water the extract was washed with water distilled under reduced pressure

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

Procedure: Poly(p-hydroxystyrene) (VP-2500, produced by Nippon Soda Co., Ltd.) (30 g) as a polyhydroxystyrene compound was dissolved in 120 g of PGMEA (propylene glycol monomethyl ether acetate). To this solution, 10.40 g of 2-cyclohexylethyl vinyl ether as a vinyl ether compound and 1.45 g of 2 mass % comphorsulfonic acid (PGMEA solution) were added thereto, and the mixture was stirred at room temperature for 2 hours. Furthermore, 1.05 g of 10 mass % triethylamine (PGMEA solution) was added and after stirring for a while, the reaction solution was transferred to a separating funnel containing 165 mL of ethyl acetate. The organic layer was washed with 200 mL of distilled water three times, and ethyl acetate was removed in an evaporator. The obtained reaction solution was added dropwise to 2 L of hexane, and the supernatant was removed. The obtained product was dissolved in 95 g of PGMEA, and the low-boiling-point solvent was removed under reduced pressure conditions to obtain 132.3 g of a PGMEA solution (28.3 mass %) of Polymer Compound (R-11). after stirring for a while the reaction solution was transferred to a separating funnel The organic layer was washed with 200 mL of distilled water three times, and ethyl acetate was removed in an evaporator The obtained reaction solution the supernatant was removed The obtained product was dissolved in 95 g of PGMEA the low-boiling-point solvent was removed under reduced pressure conditions

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

Procedure: Subsequently, 5.78 g of 2-cyclohexylethyl vinyl ether as the vinyl ether compound and 1.45 g of 2% camphorsulfonic acid (PGMEA solution) were added to Solution p-1, and the mixture was stirred at room temperature for 4 hours. After 1.05 g of 6% triethylamine (PGMEA solution) was added and the mixture was stirred for a while, the reaction solution was transferred to a separating funnel containing 165 mL of ethyl acetate, and the organic layer was washed with 200 mL of distilled water three times. The organic layer was concentrated by an evaporator to remove ethyl acetate, and this reaction solution was added dropwise in 2 L of hexane. A part of the obtained precipitate was sampled for NMR measurement, and the remaining was dissolved in 70 g of PGMEA. From the obtained solution, the low boiling point solvent was removed by an evaporator to obtain 105.6 g of a PGMEA solution (32.7 mass %) of Resin (P-1). the mixture was stirred for a while the reaction solution was transferred to a separating funnel the organic layer was washed with 200 mL of distilled water three times The organic layer was concentrated by an evaporator to remove ethyl acetate this reaction solution was added dropwise in 2 L of hexane A part of the obtained precipitate was sampled for NMR measurement the remaining was dissolved in 70 g of PGMEA From the obtained solution, the low boiling point solvent was removed by an evaporator