4-(2-phenylpropan-2-yl)phenol

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

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: To an ice cold solution of (±) cis-1-hydroxymethyl-2-phthalimidocyclopentane (1.0 g, 4.08 mmol), triphenylphosphine (1.28 g, 4.9 mmol) and 4-cumylphenol (1.04 g, 4.9 mmol) in dry tetrahydrofuran (40 ml) was added diethyl azodicarboxylate (0.77 ml, 4.9 mmol). The mixture was allowed to warm to room temperature and stirred for 48 h. The reaction was poured into ice water (200 ml) and extracted into diethyl ether (3×100 ml). The combined extracts were washed with brine, dried over sodium sulfate and concentrated in vacuo. The resulting crude product was purified by chromatography on a silica gel column eluting with 10-40% diethyl ether in petroleum ether 40-60. Pooling of pure fractions afforded the title compound as a colourless oil (0.48 g). Additional fractions afforded a further 0.76 g of product which was slightly contaminated with 4-cumylphenol. extracted into diethyl ether (3×100 ml) The combined extracts were washed with brine dried over sodium sulfate concentrated in vacuo The resulting crude product was purified by chromatography on a silica gel column eluting with 10-40% diethyl ether in petroleum ether 40-60

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

Procedure: The title compound was prepared from 4-(1-methyl-1-phenyl-ethyl)-phenol and epichlorohydrin employing the procedures as set forth in Step 1 of Example 2.

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

Procedure: A 2000 mL five neck Morton flask equipped with a bottom outlet was fitted with a mechanical stirrer, a pH probe, an aqueous sodium hydroxyde (50%) inlet tube, a Claisen adapter to which dry ice condenser was attached, and a gas inlet tube. The flask was charged with bisphenol A (71 g, 311 retool), triethylamine (0.9 mL), p-cumylphenol (2.0 g, 9 retool), methylene chloride (220 mL), and the disodium salt solution of DDDA described above. Then phosgene was introduced at a rate of 2 g/rain, while the pH was maintained at 8 by addition of caustic for 10 minutes; the pH was then raised and maintained at around 10.5 while phosgene addition continued for 10 additional minutes. The total amount of phosgene added was 40 g (400 mmol). The pH was adjusted to 11-11.5 and the organic phase was separated from the brine layer and washed with 2% hydrochloric acid (3×300 mL), and with deionized water (5×300 mL). was fitted with a mechanical stirrer was maintained at 8 by addition of caustic for 10 minutes the pH was then raised the organic phase was separated from the brine layer washed with 2% hydrochloric acid (3×300 mL)

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

Procedure: Into a 200 ml reactor thoroughly dried and purged with nitrogen, 34.15 g (316.0 mmol) of paracresol, 2.50 g of Umberist-15E (trade name, available from Organo Co.) and 20 ml of toluene were introduced. To the reactor, a solution containing 14.40 g (105.0 mmol) of 4-cumylphenol diluted with 30 ml of a toluene was dropwise added at 80° C., followed by stirring for 17 hours. After the system was cooled to room temperature, the reaction solution was filtered with washing with hexane. The resulting liquid was purified by silica gel column chromatography to obtain 10.52 g (yield: 44%) of 2-cumyl-4-methylphenol. Into a 200 ml reactor thoroughly dried were introduced was dropwise added at 80° C. the reaction solution was filtered with washing with hexane The resulting liquid was purified by silica gel column chromatography

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

Procedure: Into a 200 ml reactor thoroughly dried and purged with nitrogen, 34.15 g (316.0 mmol) of paracresol, 2.50 g of Umberist-15E (trade name, available from Organo Co.) and 20 ml of toluene were introduced. To the reactor, a solution containing 14.40 g (105.0 mmol) of 4-cumylphenol diluted with 30 ml of a toluene was dropwise added at 80° C., followed by stirring for 17 hours. After the system was cooled to room temperature, the reaction solution was filtered with washing with hexane. The resulting liquid was purified by silica gel column chromatography to obtain 10.52 g (yield: 44%) of 2-cumyl-4-methylphenol. Into a 200 ml reactor thoroughly dried were introduced was dropwise added at 80° C. the reaction solution was filtered with washing with hexane The resulting liquid was purified by silica gel column chromatography

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

Procedure: The reactor was charged with 90.7 kg of bisphenol A, methylene chloride and water in proportions to afford the listed solids percentages (i.e., percentage of product in the methylene chloride solution) and p-cumylphenol and triethylamine in proportions relative to bisphenol A similar to those in Examples 1-12. Just prior to phosgenation, the reactor was charged with 2.72 kg of 50% aqueous sodium hydroxide solution. Then phosgene was added at 68-136 kg/hr, and 50% aqueous sodium hydroxide solution was added to maintain the pH at 10.0. Phosgene was added at a substantially constant rate until 47.2 kg had been added. At a phosgene ratio of 0.5, the pH was increased to a value in the range of 10.8-11.2. This pH was maintained to a phosgene ratio of 0.8, whereupon the pH was returned to 10.0 for the duration of the phosgenation.

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

Procedure: The reactor was charged with 90.7 kg of bisphenol A, methylene chloride and water in proportions to afford the listed solids percentages (i.e., percentage of product in the methylene chloride solution) and p-cumylphenol and triethylamine in proportions relative to bisphenol A similar to those in Examples 1-12. Just prior to phosgenation, the reactor was charged with 2.72 kg of 50% aqueous sodium hydroxide solution. Then phosgene was added at 68-136 kg/hr, and 50% aqueous sodium hydroxide solution was added to maintain the pH at 10.0. Phosgene was added at a substantially constant rate until 47.2 kg had been added. At a phosgene ratio of 0.5, the pH was increased to a value in the range of 10.8-11.2. This pH was maintained to a phosgene ratio of 0.8, whereupon the pH was returned to 10.0 for the duration of the phosgenation.

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

Procedure: Run 3—1% guaiacol BPA: Methylene chloride (23 L), water (8 L), BPA (4500 g, 19.8 mol), monomethoxyBPA (55 g of the above mixture), p-cumylphenol (135 g, 0.64 mol), triethylamine (40 ml) and sodium gluconate (10 g) was charged to a 75 L reactor equipped with mechanical agitation, condenser, and caustic scrubber vent system. Phosgene (2300 g, 23.2 mol) was added at a rate of 80 g/min to the reactor while 33 wt % caustic was added at a rate to maintain pH=10. The reactor contents were purged with nitrogen then transferred to another tank and centrifuged to remove the brine layer. The organic layer containing the polymer was washed on a centrifuge train with 1N HCl and then with deionized water until residual chloride levels were <5 ppm. The polymer was isolated by steam precipitation followed by drying under hot nitrogen. The final dried resin weighed 4.1 lbs, had Mw=27652 daltons and PDI=2.5 by GPC vs PC standard, <1 ppm TEA, 0.6 ppm chloride ion, <10 ppm residual free BPA, and <0.05 ppm Fe. The glass transition temperature was determined to be 153 C. equipped with mechanical agitation, condenser, and caustic scrubber vent system was added at a rate to maintain pH=10 The reactor contents were purged with nitrogen to remove the brine layer The organic layer containing the polymer was washed on a centrifuge train with 1N HCl The polymer was isolated by steam precipitation by drying under hot nitrogen

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

Procedure: Run 3—1% guaiacol BPA: Methylene chloride (23 L), water (8 L), BPA (4500 g, 19.8 mol), monomethoxyBPA (55 g of the above mixture), p-cumylphenol (135 g, 0.64 mol), triethylamine (40 ml) and sodium gluconate (10 g) was charged to a 75 L reactor equipped with mechanical agitation, condenser, and caustic scrubber vent system. Phosgene (2300 g, 23.2 mol) was added at a rate of 80 g/min to the reactor while 33 wt % caustic was added at a rate to maintain pH=10. The reactor contents were purged with nitrogen then transferred to another tank and centrifuged to remove the brine layer. The organic layer containing the polymer was washed on a centrifuge train with 1N HCl and then with deionized water until residual chloride levels were <5 ppm. The polymer was isolated by steam precipitation followed by drying under hot nitrogen. The final dried resin weighed 4.1 lbs, had Mw=27652 daltons and PDI=2.5 by GPC vs PC standard, <1 ppm TEA, 0.6 ppm chloride ion, <10 ppm residual free BPA, and <0.05 ppm Fe. The glass transition temperature was determined to be 153 C. equipped with mechanical agitation, condenser, and caustic scrubber vent system was added at a rate to maintain pH=10 The reactor contents were purged with nitrogen to remove the brine layer The organic layer containing the polymer was washed on a centrifuge train with 1N HCl The polymer was isolated by steam precipitation by drying under hot nitrogen