4,5a,6,9,9a,9b-hexahydro-1H-dibenzofuran-4a-carbaldehyde

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

Procedure: To a solution of R-9 (500 mg, 2.06 mmol) and R-10 (337.6 mg, 2.06 mmol) in DMF (20 mL) is added oxone (758.5 mg, 1.23 mmol) and the solution is stirred at room temperature for 1 hour. The mixture is concentrated in vacuo and the residue is diluted in CH2Cl2 and is washed with saturated aqueous NaHCO3. The organics are dried with Na2SO4, filtered and concentrated in vacuo to give R-11 (787 mg). The mixture is concentrated in vacuo the residue is diluted in CH2Cl2 is washed with saturated aqueous NaHCO3 The organics are dried with Na2SO4 filtered concentrated in vacuo

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