4,4-diphenylbutan-1-ol

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

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4,4-Diphenyl-1-butanol (22.41 g, 0.099 mol) was dissolved in ether (250 mL). CBr4 (41.07 g, 0.123 mol) was added and the reaction cooled to 0° C. Triphenylphosphine (38.96 g, 0.148 mol) in ether (400 mL) was added dropwise to the reaction. The reaction was then allowed to warm to room temperature overnight. DMSO (3.51 mL) was added, and the reaction allowed to stir for 8 hours. The white precipitate was filtered and washed with ether (100 mL). The ether was removed in vacuo, and the residue washed with hexanes and filter. The hexanes were removed in vacuo, and the residue chromatographed on silica gel eluting with hexanes to give 20.72 g (72%) of desired product as an oil. to warm to room temperature overnight The white precipitate was filtered washed with ether (100 mL) The ether was removed in vacuo the residue washed with hexanes filter The hexanes were removed in vacuo the residue chromatographed on silica gel eluting with hexanes

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

Procedure: 1,1-Diphenyl-1,4-butanediol (26.62 g, 0.110 mol) was dissolved in MeOH and shaken with 20% Pd/C (1.50 g) on a Parr apparatus under an H2 atmosphere (50 psi) for 17 hours. The MeOH was removed in vacuo, and the residue chromatographed on silica gel eluting with 35% EtOAc/Hexanes gave 22.53 g (91%) of desired product. The MeOH was removed in vacuo the residue chromatographed on silica gel eluting with 35% EtOAc/Hexanes

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

Procedure: 1,1-Diphenyl-1,4-butanediol (26.62 g, 0.110 mol) was dissolved in MeOH and shaken with 20% Pd/C (1.50 g) on a Parr apparatus under an H2 atmosphere (50 psi) for 17 hours. The MeOH was removed in vacuo, and the residue chromatographed on silica gel eluting with 35% EtOAc/Hexanes gave 22.53 g (91%) of desired product. The MeOH was removed in vacuo the residue chromatographed on silica gel eluting with 35% EtOAc/Hexanes

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

Procedure: To an iced-cooled solution of 4,4-diphenyl-1-butanol (5.6 g) in dichloroethane (100 mL), 11 mL of triethylamine and 2.9 mL of methanesulfonyl chloride were added dropwise in the order mentioned. After 30 minutes of stirring, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated aqueous NaCl, dried over MgSO4, and concentrated to provide 7.5 g of the title compound. Yield 99%. extracted with ethyl acetate The extract was washed with saturated aqueous NaCl dried over MgSO4 concentrated

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

Procedure: In 70 mL of ice-cooled diethyl ether was suspended 1.9 g of lithium aluminum hydride, followed by dropwise addition of a solution of 4,4-diphenylbutyric acid (6.0 g) in diethyl ether (50 mL). After completion of dropwise addition, the mixture was refluxed for 2 hours and, then, allowed to cool. To this reaction mixture, 1.9 mL of water, 1.9 mL of 15% aqueous sodium hydroxide, and 5.7 mL of water were added in the order mentioned and the mixture was stirred at room temperature for 30 minutes. The precipitate was filtered off and the filtrate was concentrated to provide 5.6 g of the title compound. Yield 99%. After completion of dropwise addition the mixture was refluxed for 2 hours to cool The precipitate was filtered off the filtrate was concentrated

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

Procedure: In 70 mL of ice-cooled diethyl ether was suspended 1.9 g of lithium aluminum hydride, followed by dropwise addition of a solution of 4,4-diphenylbutyric acid (6.0 g) in diethyl ether (50 mL). After completion of dropwise addition, the mixture was refluxed for 2 hours and, then, allowed to cool. To this reaction mixture, 1.9 mL of water, 1.9 mL of 15% aqueous sodium hydroxide, and 5.7 mL of water were added in the order mentioned and the mixture was stirred at room temperature for 30 minutes. The precipitate was filtered off and the filtrate was concentrated to provide 5.6 g of the title compound. Yield 99%. After completion of dropwise addition the mixture was refluxed for 2 hours to cool The precipitate was filtered off the filtrate was concentrated

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

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4,4-Diphenyl-1-butanol (22.41 g, 0.099 mol) was dissolved in ether (250 mL). CBr4 (41.07 g, 0.123 mol) was added and the reaction cooled to 0° C. Triphenylphosphine (38.96 g, 0.148 mol) in ether (400 mL) was added dropwise to the reaction. The reaction was then allowed to warm to room temperature overnight. DMSO (3.51 mL) was added, and the reaction allowed to stir for 8 hours. The white precipitate was filtered and washed with ether (100 mL). The ether was removed in vacuo, and the residue washed with hexanes and filter. The hexanes were removed in vacuo, and the residue chromatographed on silica gel eluting with hexanes to give 20.72 g (72%) of desired product as an oil. to warm to room temperature overnight The white precipitate was filtered washed with ether (100 mL) The ether was removed in vacuo the residue washed with hexanes filter The hexanes were removed in vacuo the residue chromatographed on silica gel eluting with hexanes

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

Procedure: 1,1-Diphenyl-1,4-butanediol (26.62 g, 0.110 mol) was dissolved in MeOH and shaken with 20% Pd/C (1.50 g) on a Parr apparatus under an H2 atmosphere (50 psi) for 17 hours. The MeOH was removed in vacuo, and the residue chromatographed on silica gel eluting with 35% EtOAc/Hexanes gave 22.53 g (91%) of desired product. The MeOH was removed in vacuo the residue chromatographed on silica gel eluting with 35% EtOAc/Hexanes

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 825 mg (3.65 mmol) of 4,4-diphenylbutane-1-ol, 0.1 ml (0.72 mmol) of triethylamine and 0.40 ml (5.19 mmol) of diketene were stirred in 30 ml of toluene under heating at 80° C. for 4 hours. After the addition of saturated aqueous sodium hydrogencarbonate solution at room temperature followed by the extraction with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the title compound. followed by the extraction with ethyl acetate the organic layer was dried over anhydrous sodium sulfate concentrated under reduced pressure

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

Procedure: 11.2 g (46.2 mmol) of 1,1-diphenyl-1,4-butanediol was hydrogenated (45° C., 5 atm) in 100 ml of methanol in the presence of 0.5 ml of concentrated sulfuric acid and 10% palladium/carbon to obtain the title compound.