2-[2-(2-hydroxyphenyl)propan-2-yl]phenol

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

Procedure: Sodium hydride (2.60 g of 60 percent dispersion in oil) was placed in a 1 1 flask and extracted twice with pentane. To this was added first 250 ml of dimethylformamide and then, dropwise with stirring over 1 hour, 6.0 ml of ethanethiol in 40 ml of dimethylformamide. 2,2-Bis(2-methoxyphenyl)propane (8.0 g, 31 mmol) in 100 ml of dimethylformamide was then added and the mixture was heated at reflux with stirring for 24 hours and allowed to stand at ambient temperature for another approximately 18 hours. One 1 of ether was added and the resulting solution was extracted with water and twice with 4.0 N sodium hydroxide solution. The combined aqueous extracts were neutralized with concentrated hydrochloric acid to a pH of about 9-10. Ether (500 ml) was then added and, after shaking, the ether layer was separated, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain about 3 g of the title compound as a brown oil containing some dimethylformamide. The proton NMR spectrum was consistent with the assigned structure. extracted twice with pentane To this was added first 250 ml of dimethylformamide the mixture was heated at reflux with stirring for 24 hours to stand at ambient temperature for another approximately 18 hours the resulting solution was extracted with water and twice with 4.0 N sodium hydroxide solution Ether (500 ml) was then added after shaking the ether layer was separated dried over magnesium sulfate filtered concentrated by evaporation under reduced pressure

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

Procedure: Sodium hydride (2.60 g of 60 percent dispersion in oil) was placed in a 1 l flask and extracted twice with pentane. To this was added first 250 ml of dimethylformamide and then, dropwise with stirring over 1 hour, 6.0 ml of ethanethiol in 40 ml of dimethylformamide. 2,2-Bis(2-methoxyphenyl)propane (8.0 g, 31 mmol) in 100 ml of dimethylformamide was then added and the mixture was heated at reflux with stirring for 24 hours and allowed to stand at ambient temperature for another approximately 18 hours. One 1 of ether was added and the resulting solution was extracted with water and twice with 4.0N sodium hydroxide solution. The combined aqueous extracts were neutralized with concentrated hydrochloric acid to a pH of about 9-10. Ether (500 ml) was then added and, after shaking, the ether layer was separated, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain about 3 g of the title compound as a brown oil containing some dimethylformamide. The proton NMR spectrum was consistent with the assigned structure. extracted twice with pentane To this was added first 250 ml of dimethylformamide the mixture was heated at reflux with stirring for 24 hours to stand at ambient temperature for another approximately 18 hours the resulting solution was extracted with water and twice with 4.0N sodium hydroxide solution Ether (500 ml) was then added after shaking the ether layer was separated dried over magnesium sulfate filtered concentrated by evaporation under reduced pressure

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

Procedure: Sodium hydride (2.60 g of 60 percent dispersion in oil) was placed in a 1 l flask and extracted twice with pentane. To this was added first 250 ml of dimethylformamide and then, dropwise with stirring over 1 hour, 6.0 ml of ethanethiol in 40 ml of dimethylformamide. 2,2-Bis(2-methoxyphenyl)propane (8.0 g, 31 mmol) in 100 ml of dimethylformamide was then added and the mixture was heated at reflux with stirring for 24 hours and allowed to stand at ambient temperature for another approximately 18 hours. One 1 of ether was added and the resulting solution was extracted with water and twice with 4.0N sodium hydroxide solution. The combined aqueous extracts were neutralized with concentrated hydrochloric acid to a pH of about 9-10. Ether (500 ml) was then added and, after shaking, the ether layer was separated, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain about 3 g of the title compound as a brown oil containing some dimethylformamide. The proton NMR spectrum was consistent with the assigned structure. extracted twice with pentane To this was added first 250 ml of dimethylformamide the mixture was heated at reflux with stirring for 24 hours to stand at ambient temperature for another approximately 18 hours the resulting solution was extracted with water and twice with 4.0N sodium hydroxide solution Ether (500 ml) was then added after shaking the ether layer was separated dried over magnesium sulfate filtered concentrated by evaporation under reduced pressure

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

Procedure: Sodium hydride (2.60 g of 60 percent dispersion in oil) was placed in a 1 1 flask and extracted twice with pentane. To this was added first 250 ml of dimethylformamide and then, dropwise with stirring over 1 hour, 6.0 ml of ethanethiol in 40 ml of dimethylformamide. 2,2-Bis(2-methoxyphenyl)propane (8.0 g, 31 mmol) in 100 ml of dimethylformamide was then added and the mixture was heated at reflux with stirring for 24 hours and allowed to stand at ambient temperature for another approximately 18 hours. One 1 of ether was added and the resulting solution was extracted with water and twice with 4.0 N sodium hydroxide solution. The combined aqueous extracts were neutralized with concentrated hydrochloric acid to a pH of about 9-10. Ether (500 ml) was then added and, after shaking, the ether layer was separated, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain about 3 g of the title compound as a brown oil containing some dimethylformamide. The proton NMR spectrum was consistent with the assigned structure. extracted twice with pentane To this was added first 250 ml of dimethylformamide the mixture was heated at reflux with stirring for 24 hours to stand at ambient temperature for another approximately 18 hours the resulting solution was extracted with water and twice with 4.0 N sodium hydroxide solution Ether (500 ml) was then added after shaking the ether layer was separated dried over magnesium sulfate filtered concentrated by evaporation under reduced pressure

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

Procedure: Sodium hydride (2.60 g of 60 percent dispersion in oil) was placed in a 1 1 flask and extracted twice with pentane. To this was added first 250 ml of dimethylformamide and then, dropwise with stirring over 1 hour, 6.0 ml of ethanethiol in 40 ml of dimethylformamide. 2,2-Bis(2-methoxyphenyl)propane (8.0 g, 31 mmol) in 100 ml of dimethylformamide was then added and the mixture was heated at reflux with stirring for 24 hours and allowed to stand at ambient temperature for another approximately 18 hours. One 1 of ether was added and the resulting solution was extracted with water and twice with 4.0N sodium hydroxide solution. The combined aqueous extracts were neutralized with concentrated hydrochloric acid to a pH of about 9-10. Ether (500 ml) was then added and, after shaking, the ether layer was separated, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain about 3 g of the title compound as a brown oil containing some dimethylformamide. The proton NMR spectrum was consistent with the assigned structure. extracted twice with pentane To this was added first 250 ml of dimethylformamide the mixture was heated at reflux with stirring for 24 hours to stand at ambient temperature for another approximately 18 hours the resulting solution was extracted with water and twice with 4.0N sodium hydroxide solution Ether (500 ml) was then added after shaking the ether layer was separated dried over magnesium sulfate filtered concentrated by evaporation under reduced pressure

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

Procedure: Sodium hydride (2.60 g of 60 percent dispersion in oil) was placed in a 1 l flask and extracted twice with pentane. To this was added first 250 ml of dimethylformamide and then, dropwise with stirring over 1 hour, 6.0 ml of ethanethiol in 40 ml of dimethylformamide. 2,2-Bis(2-methoxyphenyl)propane (8.0 g, 31 mmol) in 100 ml of dimethylformamide was then added and the mixture was heated at reflux with stirring for 24 hours and allowed to stand at ambient temperature for another approximately 18 hours. One 1 of ether was added and the resulting solution was extracted with water and twice with 4.0N sodium hydroxide solution. The combined aqueous extracts were neutralized with concentrated hydrochloric acid to a pH of about 9-10. Ether (500 ml) was then added and, after shaking, the ether layer was separated, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain about 3 g of the title compound as a brown oil containing some dimethylformamide. The proton NMR spectrum was consistent with the assigned structure. extracted twice with pentane To this was added first 250 ml of dimethylformamide the mixture was heated at reflux with stirring for 24 hours to stand at ambient temperature for another approximately 18 hours the resulting solution was extracted with water and twice with 4.0N sodium hydroxide solution Ether (500 ml) was then added after shaking the ether layer was separated dried over magnesium sulfate filtered concentrated by evaporation under reduced pressure

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

Procedure: A mixture of 2,2'-isopropylidene bisphenol (3.65 g, 0.01594 mol), potassium hydroxide (2.68 g of 85 percent, 0.0478 mol) and dichloroacetic acid (1.31 ml, 0.01594 mol) in 65 ml cf isopropyl alcohol is heated at reflux. After 20 hours at reflux, an additional 1.79 g of 85 percent KOH and 1.31 ml of dichloroacetic acid are added and the reaction mixture is heated at reflux for 2 days. The reaction mixture is then diluted with 200 ml of H2O, acidified by the addition of concentrated HC1 (10 ml) and extracted into ethyl acetate. The ethyl acetate solution is washed with brine, dried over MgSO4 and concentrated. The residue is washed with petroleum ether to afford 3.7 g of crude product as a red-brown syrup. This material is then purified by an esterification-saponification-esterification procedure (esterification agent methanol, H2SO4). Dry column chromatography yields 0.97 g of crude product, which is saponified (NaOH, MeOH-H2O ), and purified by dry column chromatography to afford 0.60 g of a white solid. Esterification of this material (EtOH, H2SO4) and purification by preparative thin layer chromatography (elution with 1:4 ethyl acetate-hexanes) yields 0.25 g of product as a clear syrup: IR (neat) 3.34, 5.65, 6.95, 8.2, 13.2 cm-1; 1H NMR (CDCl3) δ1.28 (t, 3, CH2CH3), 1.75 and 1.9 (2s, 6, (CH3)2C), 4.24 (q, 2 CH2CH3), (s, 1, CH), 6.9-7.6 (m, 8, Ar--H); m/e 312. is heated at reflux After 20 hours at reflux the reaction mixture is heated at reflux for 2 days acidified by the addition of concentrated HC1 (10 ml) extracted into ethyl acetate The ethyl acetate solution is washed with brine dried over MgSO4 concentrated The residue is washed with petroleum ether to afford 3.7 g of crude product as a red-brown syrup This material is then purified by an esterification-saponification-esterification procedure (esterification agent methanol, H2SO4) Dry column chromatography yields 0.97 g of crude product, which purified by dry column chromatography

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

Procedure: Sodium hydride (2.60 g of 60 percent dispersion in oil) was placed in a 1 l flask and extracted twice with pentane. To this was added first 250 ml of dimethylformamide and then, dropwise with stirring over 1 hour, 6.0 ml of ethanethiol in 40 ml of dimethylformamide. 2,2-Bis(2-methoxyphenyl)propane (8.0 g, 31 mmol) in 100 ml of dimethylformamide was then added and the mixture was heated at reflux with stirring for 24 hours and allowed to stand at ambient temperature for another approximately 18 hours. One 1 of ether was added and the resulting solution was extracted with water and twice with 4.0N sodium hydroxide solution. The combined aqueous extracts were neutralized with concentrated hydrochloric acid to a pH of about 9-10. Ether (500 ml) was then added and, after shaking, the ether layer was separated, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain about 3 g of the title compound as a brown oil containing some dimethylformamide. The proton NMR spectrum was consistent with the assigned structure. extracted twice with pentane To this was added first 250 ml of dimethylformamide the mixture was heated at reflux with stirring for 24 hours to stand at ambient temperature for another approximately 18 hours the resulting solution was extracted with water and twice with 4.0N sodium hydroxide solution Ether (500 ml) was then added after shaking the ether layer was separated dried over magnesium sulfate filtered concentrated by evaporation under reduced pressure

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

Procedure: Sodium hydride (2.60 g of 60 percent dispersion in oil) was placed in a 1 1 flask and extracted twice with pentane. To this was added first 250 ml of dimethylformamide and then, dropwise with stirring over 1 hour, 6.0 ml of ethanethiol in 40 ml of dimethylformamide. 2,2-Bis(2-methoxyphenyl)propane (8.0 g, 31 mmol) in 100 ml of dimethylformamide was then added and the mixture was heated at reflux with stirring for 24 hours and allowed to stand at ambient temperature for another approximately 18 hours. One 1 of ether was added and the resulting solution was extracted with water and twice with 4.0 N sodium hydroxide solution. The combined aqueous extracts were neutralized with concentrated hydrochloric acid to a pH of about 9-10. Ether (500 ml) was then added and, after shaking, the ether layer was separated, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain about 3 g of the title compound as a brown oil containing some dimethylformamide. The proton NMR spectrum was consistent with the assigned structure. extracted twice with pentane To this was added first 250 ml of dimethylformamide the mixture was heated at reflux with stirring for 24 hours to stand at ambient temperature for another approximately 18 hours the resulting solution was extracted with water and twice with 4.0 N sodium hydroxide solution Ether (500 ml) was then added after shaking the ether layer was separated dried over magnesium sulfate filtered concentrated by evaporation under reduced pressure