(2,3,5-trichlorophenyl)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:

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

Procedure: A solution of 7.6 grams (0.028 mole) of phosphorus tribromide in 200 mL of toluene was stirred, and 17.0 grams (0.080 mole) of 2,3,5-trichlorophenylmethanol was washed into the reaction vessel with about 5 mL of toluene. Upon completion of addition, the reaction mixture was stirred at ambient temperature for about 16 hours. The reaction mixture was then concentrated under reduced pressure to a residue. The residue was dissolved in ethyl acetate and washed with three portions of water. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 21.2 grams of 2,3,5-trichlorophenylmethyl bromide. The NMR spectrum was consistent with the proposed structure. Upon completion of addition The reaction mixture was then concentrated under reduced pressure to a residue The residue was dissolved in ethyl acetate washed with three portions of water The organic layer was dried with sodium sulfate filtered The filtrate was concentrated under reduced pressure

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

Procedure: A solution of 7.6 grams (0.028 mole) of phosphorus tribromide in 200 mL of toluene was stirred, and 17.0 grams (0.080 mole) of 2,3,5-trichlorophenylmethanol was washed into the reaction vessel with about 5 mL of toluene. Upon completion of addition, the reaction mixture was stirred at ambient temperature for about 16 hours. The reaction mixture was then concentrated under reduced pressure to a residue. The residue was dissolved in ethyl acetate and washed with three portions of water. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 21.2 grams of 2,3,5-trichlorophenylmethyl bromide. The NMR spectrum was consistent with the proposed structure. Upon completion of addition The reaction mixture was then concentrated under reduced pressure to a residue The residue was dissolved in ethyl acetate washed with three portions of water The organic layer was dried with sodium sulfate filtered The filtrate was concentrated under reduced pressure

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

Procedure: A suspension of 5.5 grams (0.144 mole) of lithium aluminum hydride in 300 mL of diethyl ether was stirred, and 25.0 grams (0.111 mole) of 2,3,5-trichlorobenzoic acid in 200 mL of diethyl ether was added dropwise at a rate which maintained a gentle reflux. The complete addition required about 75 minutes. Upon completion of addition, the reaction was mixture heated at reflux for 4.5 hours. After this time the reaction mixture was stirred for about 16 hours, during which time it was allowed to cool to ambient temperature. The reaction mixture was then cooled to below 10° C., and 6 mL of water was added slowly dropwise. Upon completion of addition, 5 mL of aqueous 20% sodium hydroxide was added dropwise, followed by an additional 12 mL of water added dropwise. The reaction mixture was then stirred for 20 minutes and filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure to a residue. The residue was stirred into water, and the combination was extracted with ethyl acetate. The extracts were combined and washed with three portions of water. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 17.1 grams of 2,3,5-trichlorophenylmethanol. The NMR spectrum was consistent with the proposed structure. maintained a gentle reflux The complete addition required about 75 minutes Upon completion of addition heated at reflux for 4.5 hours After this time the reaction mixture was stirred for about 16 hours, during which time it The reaction mixture was then cooled to below 10° C. was added dropwise added dropwise The reaction mixture was then stirred for 20 minutes filtered through diatomaceous earth The filtrate was concentrated under reduced pressure to a residue The residue was stirred into water the combination was extracted with ethyl acetate washed with three portions of water The organic layer was dried with sodium sulfate filtered The filtrate was concentrated under reduced pressure

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

Procedure: A suspension of 5.5 grams (0.144 mole) of lithium aluminum hydride in 300 mL of diethyl ether was stirred, and 25.0 grams (0.111 mole) of 2,3,5-trichlorobenzoic acid in 200 mL of diethyl ether was added dropwise at a rate which maintained a gentle reflux. The complete addition required about 75 minutes. Upon completion of addition, the reaction was mixture heated at reflux for 4.5 hours. After this time the reaction mixture was stirred for about 16 hours, during which time it was allowed to cool to ambient temperature. The reaction mixture was then cooled to below 10° C., and 6 mL of water was added slowly dropwise. Upon completion of addition, 5 mL of aqueous 20% sodium hydroxide was added dropwise, followed by an additional 12 mL of water added dropwise. The reaction mixture was then stirred for 20 minutes and filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure to a residue. The residue was stirred into water, and the combination was extracted with ethyl acetate. The extracts were combined and washed with three portions of water. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 17.1 grams of 2,3,5-trichlorophenylmethanol. The NMR spectrum was consistent with the proposed structure. maintained a gentle reflux The complete addition required about 75 minutes Upon completion of addition heated at reflux for 4.5 hours After this time the reaction mixture was stirred for about 16 hours, during which time it The reaction mixture was then cooled to below 10° C. was added dropwise added dropwise The reaction mixture was then stirred for 20 minutes filtered through diatomaceous earth The filtrate was concentrated under reduced pressure to a residue The residue was stirred into water the combination was extracted with ethyl acetate washed with three portions of water The organic layer was dried with sodium sulfate filtered The filtrate was concentrated under reduced pressure

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

Procedure: To a solution of 2,3,5-trichlorobenzaldehyde (Aldrich, 50 gms) in ethanol (1.0 L) at room temperature was added NaBH4 (7.00 gms) and the resulting mixture stirred for 3.5 hours. The reaction was quenched with water, and the solvent evaporated in vacuo before partitioning the residue between CHCl3 and saturated NaHCO3 solution. The organic phase was washed with brine, dried over MgSO4, filtered and the solvent evaporated in vacuo to leave a white solid. 43.00 gms, mp.90°-93° C. The reaction was quenched with water the solvent evaporated in vacuo before partitioning the residue between CHCl3 and saturated NaHCO3 solution The organic phase was washed with brine dried over MgSO4 filtered the solvent evaporated in vacuo to leave a white solid

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

Procedure: To a solution of 2,3,5-trichlorobenzaldehyde (Aldrich, 50 gms) in ethanol (1.0 L) at room temperature was added NaBH4 (7.00 gms) and the resulting mixture stirred for 3.5 hours. The reaction was quenched with water, and the solvent evaporated in vacuo before partitioning the residue between CHCl3 and saturated NaHCO3 solution. The organic phase was washed with brine, dried over MgSO4, filtered and the solvent evaporated in vacuo to leave a white solid. 43.00 gms, mp. 90°-93° C. The reaction was quenched with water the solvent evaporated in vacuo before partitioning the residue between CHCl3 and saturated NaHCO3 solution The organic phase was washed with brine dried over MgSO4 filtered the solvent evaporated in vacuo to leave a white solid

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

Procedure: To a solution of 2,3,5-trichlorobenzaldehyde (Aldrich, 50 gms) in ethanol (1.0L) at room temperature was added NaBH4 (7.00 gms) and the resulting mixture stirred for 3.5 hours. The reaction was quenched with water, and the solvent evaporated in vacuo before partitioning the residue between CHCl3 and saturated NaHCO3 solution. The organic phase was washed with brine, dried over MgSO4, filtered and the solvent evaporated in vacuo to leave a white solid. 43.00 gms, mp. 90°-93° C. The reaction was quenched with water the solvent evaporated in vacuo before partitioning the residue between CHCl3 and saturated NaHCO3 solution The organic phase was washed with brine dried over MgSO4 filtered the solvent evaporated in vacuo to leave a white solid

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

Procedure: To a solution of 2,3,5-trichlorobenzaldehyde (Aldrich, 50 gms) in ethanol (1.0 L) at room temperature was added NaBH4 (7.00 gms) and the resulting mixture stirred for 3.5 hours. The reaction was quenched with water, and the solvent evaporated in vacuo before partitioning the residue between CHCl3 and saturated NaHCO3 solution. The organic phase was washed with brine, dried over MgSO4, filtered and the solvent evaporated in vacuo to leave a white solid. 43.00 gms, mp. 90°-93° C. The reaction was quenched with water the solvent evaporated in vacuo before partitioning the residue between CHCl3 and saturated NaHCO3 solution The organic phase was washed with brine dried over MgSO4 filtered the solvent evaporated in vacuo to leave a white solid