5-phenylpentan-2-ol

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 a stirred solution of 5-phenyl-2-pentanol (482 g.; 2.94 moles) in tetrahydrofuran (2250 ml.) at 0° C. was added methanesulfonyl chloride (300 ml.) at such a rate that the internal temperature does not rise above 10° C. (total addition time 4.5 hours). After addition is complete, the reaction mixture was allowed to warm to room temperature and stirring was continued for an additional hour. The reaction mixture was filtered and the supernate concentrated to a light yellow oil (2800 g.) which was dissolved in chloroform (2 liters) and washed with water (4×1 liter), brine (1×1 liter), charcoal treated (50 g.), dried (MgSO4), filtered through diatomaceous earth and concentrated to a light orange oil (687 g., 95% yield). This material was suitable for use without further purification. does not rise above 10° C. (total addition time 4.5 hours) After addition was continued for an additional hour The reaction mixture was filtered the supernate concentrated to a light yellow oil (2800 g.) which was dissolved in chloroform (2 liters) washed with water (4×1 liter), brine (1×1 liter), charcoal treated (50 g.) dried (MgSO4) filtered through diatomaceous earth concentrated to a light orange oil (687 g., 95% yield) This material was suitable for use without further purification

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In one portion, 3.6 ml (4.72 g, 23.7 mmol) of 3-phenylpropyl bromide are added to a suspension of 5.2 g (213 mmol) of magnesium in 30 ml of diethyl ether. A further 30 ml (39.3 g, 197 mmol) of 3-phenylpropyl bromide are added dropwise at such a rate that constant reflux is maintained. After the addition has ended, the mixture is diluted with 100 ml of diethyl ether and refluxed for 30 min. The mixture is diluted with a further 80 ml of diethyl ether and cooled to −78° C. A solution, of a temperature of 0° C., of 19 ml of acetaldehyde in 50 ml of ether is added dropwise, and the reaction mixture is stirred at −78° C. for 2 hours and warmed to room temperature. 50 ml of saturated NH4Cl solution are added and the organic phase is extracted with 1N HCl and saturated NaHCO3 solution and dried over Na2SO4. Removal of the solvent gives 33.4 g (95%) of a slightly yellow oil. that constant reflux is maintained After the addition refluxed for 30 min warmed to room temperature the organic phase is extracted with 1N HCl and saturated NaHCO3 solution dried over Na2SO4 Removal of the solvent gives 33.4 g (95%) of a slightly yellow oil

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

Procedure: To phosphorus pentabromide, prepared by addition of bromine (9.0 g.) in methylene chloride (10 ml.) to phosphorous tribromide (15.0 g.) in methylene chloride (15 ml.) at 0° C., is added 5-phenyl-2-pentanol (8.2 g.) in metnhylene chloride at 0° C. The mixture is stirred for 2.5 hours at 0° C. and is then allowed to warm to room temperature. Water (50 ml.) is added, the mixture stirred for 1 hour and the methylene chloride layer separated. The extraction is repeated and the combined extracts washed with water, saturated sodium bicarbonate solution, brine and then dried over magnesium sulfate. Concentration of the dried extracts gives 12.4 g. of title product as a light yellow oil. to warm to room temperature the mixture stirred for 1 hour the methylene chloride layer separated The extraction the combined extracts washed with water, saturated sodium bicarbonate solution, brine dried over magnesium sulfate Concentration of the dried extracts gives 12.4 g

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

Procedure: To phosphorus pentabromide, prepared by addition of bromine (9.0 g.) in methylene chloride (10 ml.) to phosphorous tribromide (15.0 g.) in methylene chloride (15 ml.) at 0° C., is added 5-phenyl-2-pentanol (8.2 g.) in metnhylene chloride at 0° C. The mixture is stirred for 2.5 hours at 0° C. and is then allowed to warm to room temperature. Water (50 ml.) is added, the mixture stirred for 1 hour and the methylene chloride layer separated. The extraction is repeated and the combined extracts washed with water, saturated sodium bicarbonate solution, brine and then dried over magnesium sulfate. Concentration of the dried extracts gives 12.4 g. of title product as a light yellow oil. to warm to room temperature the mixture stirred for 1 hour the methylene chloride layer separated The extraction the combined extracts washed with water, saturated sodium bicarbonate solution, brine dried over magnesium sulfate Concentration of the dried extracts gives 12.4 g

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

Procedure: To a stirred solution of 5-phenyl-2-pentanol (482 g.; 2.94 moles) in tetrahydrofuran (2250 ml.) at 0° C. was added methanesulfonyl chloride (300 ml.) at such a rate that the internal temperature does not rise above 10° C. (total addition time 4.5 hours). After addition is complete, the reaction mixture was allowed to warm to room temperature and stirring was continued for an additional hour. The reaction mixture was filtered and the supernate concentrated to a light yellow oil (2800 g.) which was dissolved in chloroform (2 liters) and washed with water (4×1 liter), brine (1×1 liter), charcoal treated (50 g.), dried (MgSO4), filtered through diatomaceous earth and concentrated to a light orange oil (687 g., 95% yield). This material was suitable for use without further purification. does not rise above 10° C. (total addition time 4.5 hours) After addition was continued for an additional hour The reaction mixture was filtered the supernate concentrated to a light yellow oil (2800 g.) which was dissolved in chloroform (2 liters) washed with water (4×1 liter), brine (1×1 liter), charcoal treated (50 g.) dried (MgSO4) filtered through diatomaceous earth concentrated to a light orange oil (687 g., 95% yield) This material was suitable for use without further purification

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

Procedure: To phosphorous pentabromide, prepared by addition of bromine (9.0 g.) in methylene chloride (10 ml.) to phosphorous tribromide (15.0 g.) in methylene chloride (15 ml.) at 0° C., is added 5-phenyl-2-pentanol (812 g.) in methylene chloride at 0° C. The mixture is stirred for 2.5 hours at 0° C. and is then allowed to warm to room temperature. Water (50 ml.) is added, the mixture stirred for one hour and the methylene chloride layer separated. The extraction is repeated and the combined extracts washed with water, saturated sodium bicarbonate solution, brine and then dried over magnesium sulfate. Concentration of the dried extracts gives 12.4 g. of title product as a light yellow oil. to warm to room temperature the mixture stirred for one hour the methylene chloride layer separated The extraction the combined extracts washed with water, saturated sodium bicarbonate solution, brine dried over magnesium sulfate Concentration of the dried extracts gives 12.4 g

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

Procedure: To phosphorous pentabromide, prepared by addition of bromine (9.0 g.) in methylene chloride (10 ml.) to phosphorous tribromide (15.0 g.) in methylene chloride (15 ml.) at 0° C., is added 5-phenyl-2-pentanol (812 g.) in methylene chloride at 0° C. The mixture is stirred for 2.5 hours at 0° C. and is then allowed to warm to room temperature. Water (50 ml.) is added, the mixture stirred for one hour and the methylene chloride layer separated. The extraction is repeated and the combined extracts washed with water, saturated sodium bicarbonate solution, brine and then dried over magnesium sulfate. Concentration of the dried extracts gives 12.4 g. of title product as a light yellow oil. to warm to room temperature the mixture stirred for one hour the methylene chloride layer separated The extraction the combined extracts washed with water, saturated sodium bicarbonate solution, brine dried over magnesium sulfate Concentration of the dried extracts gives 12.4 g

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

Procedure: To phosphorous pentabromide, prepared by addition of bromine (9.0 g.) in methylene chloride (10 ml.) to phosphorous tribromide (15.0 g.) in methylene chloride (15 ml.) at 0° C., is added 5-phenyl-2-pentanol (812 g.) in methylene chloride at 0° C. The mixture is stirred for 2.5 hours at 0° C. and is then allowed to warm to room temperature. Water (50 ml.) is added, the mixture stirred for one hour and the methylene chloride layer separated. The extraction is repeated and the combined extracts washed with water, saturated sodium bicarbonate solution, brine and then dried over magnesium sulfate. Concentration of the dried extracts gives 12.4 g. of title product as a light yellow oil. to warm to room temperature the mixture stirred for one hour the methylene chloride layer separated The extraction the combined extracts washed with water, saturated sodium bicarbonate solution, brine dried over magnesium sulfate Concentration of the dried extracts gives 12.4 g

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

Procedure: To a stirred solution of 5-phenyl-2-pentanol (482 g.; 2.94 moles) in tetrahydrofuran (2250 ml.) at 0° C. was added methanesulfonyl chloride (300 ml.) at such a rate that the internal temperature does not rise above 10° C. (total addition time 4.5 hours). After addition is complete, the reaction mixture was allowed to warm to room temperature and stirring was continued for an additional hour. The reaction mixture was filtered and the supernate concentrated to a light yellow oil (2800 g.) which was dissolved in chloroform (2 liters) and washed with water (4×1 liter), brine (1×1 liter), charcoal treated (50 g.), dried (MgSO4), filtered through diatomaceous earth and concentrated to a light orange oil (687 g., 95% yield). This material was suitable for use without further purification. does not rise above 10° C. (total addition time 4.5 hours) After addition was continued for an additional hour The reaction mixture was filtered the supernate concentrated to a light yellow oil (2800 g.) which was dissolved in chloroform (2 liters) washed with water (4×1 liter), brine (1×1 liter), charcoal treated (50 g.) dried (MgSO4) filtered through diatomaceous earth concentrated to a light orange oil (687 g., 95% yield) This material was suitable for use without further purification

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