[2-(4-fluorophenoxy)phenyl]methanol

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: 8.5 g of thionyl chloride are added dropwise over a 10 minutes span to a stirring mixture of 13.0 g of 2-(4-fluorophenoxy)benzyl alcohol in 80 Ml of benzene at ambient temperature. After total addition, the reaction mixture is stirred for 16 hours before being carefully poured onto 350 ml of crushed ice containing 8 ml of sodium bicarbonate. The mixture is stirred until the ice melts. The layers separate and the benzene layer is successively washed twice with 40 ml portions of a half saturated sodium bicarbonate solution, washed twice with 40 ml portions of water, washed once with 25 ml saturated sodium chloride solution, dried and rotary evaporated to provide a clear liquid. The liquid is distilled at 106°-109° C. and 0.16 mm to provide a clear colorless liquid of 2-(4-fluorophenoxy)benzyl chloride. After total addition The layers separate the benzene layer is successively washed twice with 40 ml portions of a half saturated sodium bicarbonate solution washed twice with 40 ml portions of water washed once with 25 ml saturated sodium chloride solution dried rotary evaporated to provide a clear liquid The liquid is distilled at 106°-109° C.

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

Procedure: 36.1 ml of 70% sodium-bis-(2-methoxyethoxy) aluminum hydride in benzene are added dropwise over a one hour span to a stirring mixture of 15 g of 2-(4-fluorophenoxy)benzoic acid in 150 ml of benzene under nitrogen at ambient temperature. After total addition, the reaction mixture is stirred for an additional 30 minutes and then permitted to stand for 4 days. Thereafter, the reaction mixture is cooled to 0° C. before adding 100 mls of 10% sodium hydroxide while stirring. Following this addition, the layers separate and the aqueous layer is extracted twice with 100 ml portions of benzene. The combined benzene solutions are successively washed twice with 100 ml portions of water, washed once with 60 ml of saturated sodium chloride solution and dried, providing a clear yellow oil. The oil is distilled at 118.5°-121.5° C. and 0.07 mm pressure to provide the clear, colorless liquid, 2-(4-fluorophenoxy)benzyl alcohol. After total addition to stand for 4 days while stirring this addition the layers separate the aqueous layer is extracted twice with 100 ml portions of benzene The combined benzene solutions are successively washed twice with 100 ml portions of water washed once with 60 ml of saturated sodium chloride solution dried providing a clear yellow oil The oil is distilled at 118.5°-121.5° C.

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

Procedure: 8.5 g of thionyl chloride are added dropwise over a 10 minutes span to a stirring mixture of 13.0 g of 2-(4-fluorophenoxy)benzyl alcohol in 80 ml of benzene at ambient temperature. After total addition, the reaction mixture is stirred for 16 hours before being carefully poured onto 350 ml of crushed ice containing 8 ml of sodium bicarbonate. The mixture is stirred until the ice melts. The layers separate and the benzene layer is successively washed twice with 40 ml portions of a half saturated sodium bicarbonate solution, washed twice with 40 ml portions of water, washed once with a 25 ml portion of a saturated sodium chloride solution, dried and rotary evaporated to provide a clear liquid. The liquid is distilled at 106°-109° C. and 0.16 mm to provide a clear colorless liquid of 2-(4-fluorophenoxy)benzyl chloride. After total addition The layers separate the benzene layer is successively washed twice with 40 ml portions of a half saturated sodium bicarbonate solution washed twice with 40 ml portions of water washed once with a 25 ml portion of a saturated sodium chloride solution dried rotary evaporated to provide a clear liquid The liquid is distilled at 106°-109° C.

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

Procedure: 36.1 mls of 70% sodium-(2-methoxyethyl)aluminum hydride in benzene are added dropwise over a one hour span to a stirring mixture of 15 g of 2-(4-fluorophenoxy)benzoic acid in 150 ml of benzene under nitrogen at ambient temperature. After total addition, the reaction mixture is stirred for an additional 30 minutes and then permitted to stand for 4 days. Thereafter, the reaction mixture is cooled to 0° C. before 100 mls of 10% sodium hydroxide are added with stirring. Following this addition, the layers separate and the aqueous layer is extracted twice with 100 ml portions of benzene. The combined benzene solutions are successively washed twice with 100 ml portions of water, washed once with 60 ml of a saturated sodium chloride solution and dried, providing a clear yellow oil. The oil is distilled at 118.5°-121.5° C. and 0.07 mm pressure to provide the clear, colorles liquid, 2-(4-fluorophenoxy)benzyl alcohol. After total addition to stand for 4 days are added with stirring this addition the layers separate the aqueous layer is extracted twice with 100 ml portions of benzene The combined benzene solutions are successively washed twice with 100 ml portions of water washed once with 60 ml of a saturated sodium chloride solution dried providing a clear yellow oil The oil is distilled at 118.5°-121.5° C.