1-phenoxypropan-2-one

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: To a stirred solution of 24.2 g (0.16 mole) of phenoxy-2-propanone (Eastman) in 150 mL of dry ethyl ether was added 56 ml (0.17 mole) of methylmagnesium bromide (3.0M solution in ethyl ether, Aldrich) and the reaction mixture was stirred at ambient temperature under a nitrogen atmosphere for 4 hr. The reaction mixture was treated with 100 ml of saturated ammonium chloride solution and vigorously stirred for 1 hr. The layers were separated and the organic layer was washed twice with 200 ml portions of water, dried (magnesium sulfate) and the solvent evaporated under reduced pressure to yield 24.3 g (91%) of a vicous oil. A 2.3 g sample of the oil was purified by high pressure liquid chromatography (Waters Associates Prep LC/System 500 A, PrePAK 500/silica, ethyl acetate-hexanes, 1:20, flow rate 150 ml/min). The desired fractions were combined and the solvents evaporated under reduced pressure to yield 2.1 g (91% recovery) of the title compound as a colorless liquid. vigorously stirred for 1 hr The layers were separated the organic layer was washed twice with 200 ml portions of water dried (magnesium sulfate) the solvent evaporated under reduced pressure

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

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

Procedure: Phenoxy-2-propanone (0.10 mol), N-bromosuccinimide (0.10 mol) and a catalytic amount of 2,2'-azobis(2-methylpropionitrile) were stirred together in tetrachloromethane (100 ml) at 80° C. for 61/2 hours. The solvent was distilled off and the residue distilled under vacuum to give (1-bromo-2-oxopropyl) oxybenzene. Yield: 10.4 g (45 %), b.p. 66°-68° C./0.01 mm Hg. 1H NMR (CDCl3, δ): 2.50 (s, CH3) 6.40 (s, --CHBr--), 6.9-7.5 (5H, Ph). The solvent was distilled off the residue distilled under vacuum

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

Procedure: Phenoxy-2-propanone (0.10 mol), N-bromosuccinimide (0.10 mol) and a catalytic amount of 2,2'-azobis(2-methylpropionitrile) were stirred together in tetrachloromethane (100 ml) at 80° C. for 61/2 hours. The solvent was distilled off and the residue distilled under vacuum to give (1-bromo-2-oxopropyl) oxybenzene. Yield: 10.4 g (45 %), b.p. 66°-68° C./0.01 mm Hg. 1H NMR (CDCl3, δ): 2.50 (s, CH3) 6.40 (s, --CHBr--), 6.9-7.5 (5H, Ph). The solvent was distilled off the residue distilled under vacuum

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

Procedure: Phenoxy-2-propanone (3.4 mL, 25 mmol) was dissolved in ethanol (30 mL) and cooled to 0° C. Sodium borohydride (0.95 g; 25 mmol; 1 equiv.) was added. The mixture was stirred and allowed to warm to room temperature overnight. All of the starting material was gone according to tlc analysis, so the mixture was poured into water (30 mL) and ether (30 mL). The layers were separated and the aqueous layer was extracted with ether (2×20 mL). The organic layers were combined and concentrated. The resulting aqueous residue was poured into ether (25 mL). The organic layer was removed, dried (MgSO4), and concentrated to provide 1e (3.2 g; 85%). 1H nmr (300 MHz, CDCl3): 7.332-7.261 (3H, m); 6.995-6.904 (2H, m); 4.15-4.24 (1H, m); 3.972-3.768 (2H, m); 1.559 (1H, s); 1.290 (3H, d, J=6.38 Hz). IR (neat film, cm-1): 3350 (b, s); 2900 (s); 1590 (m). EIMS (m/e): 152 (M+). to warm to room temperature overnight The layers were separated the aqueous layer was extracted with ether (2×20 mL) concentrated The resulting aqueous residue was poured into ether (25 mL) The organic layer was removed dried (MgSO4) concentrated

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

Procedure: Phenoxy-2-propanone (3.4 mL, 25 mmol) was dissolved in ethanol (30 mL) and cooled to 0° C. Sodium borohydride (0.95 g; 25 mmol; 1 equiv.) was added. The mixture was stirred and allowed to warm to room temperature overnight. All of the starting material was gone according to tlc analysis, so the mixture was poured into water (30 mL) and ether (30 mL). The layers were separated and the aqueous layer was extracted with ether (2×20 mL). The organic layers were combined and concentrated. The resulting aqueous residue was poured into ether (25 mL). The organic layer was removed, dried (MgSO4), and concentrated to provide 1e (3.2 g; 85%). 1H nmr (300 MHz, CDCl3): 7.332-7.261 (3H, m); 6.995-6.904 (2H, m); 4.15-4.24 (1H, m); 3.972-3.768 (2H, m); 1.559 (1H, s); 1.290 (3H, d, J=6.38 Hz). IR (neat film, cm-1): 3350 (b, s); 2900 (s); 1590 (m). EIMS (m/e): 152 (M+). to warm to room temperature overnight The layers were separated the aqueous layer was extracted with ether (2×20 mL) concentrated The resulting aqueous residue was poured into ether (25 mL) The organic layer was removed dried (MgSO4) concentrated

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

Procedure: 0.2 mol of phenoxyacetone in 200 ml of tetrahydrofuran is saturated at reflux temperature with ammonia gas with the addition of 0.2 g of p-toluene sulphonic acid. The mixture is allowed to stand at room temperature for 24 hours and the solvent is then removed by evaporation in vacuo. The evaporation residue is employed crude in the reaction of Example 5B. the solvent is then removed by evaporation in vacuo in the reaction of Example 5B

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

Procedure: To a stirred solution of 24.2 g (0.16 mole) of phenoxy-2-propanone (Eastman) in 150 mL of dry ethyl ether was added 56 ml (0.17 mole) of methylmagnesium bromide (3.0M solution in ethyl ether, Aldrich) and the reaction mixture was stirred at ambient temperature under a nitrogen atmosphere for 4 hr. The reaction mixture was treated with 100 ml of saturated ammonium chloride solution and vigorously stirred for 1 hr. The layers were separated and the organic layer was washed twice with 200 ml portions of water, dried (magnesium sulfate) and the solvent evaporated under reduced pressure to yield 24.3 g (91%) of a vicous oil. A 2.3 g sample of the oil was purified by high pressure liquid chromatography (Waters Associates Prep LC/System 500 A, PrePAK 500/silica, ethyl acetate-hexanes, 1:20, flow rate 150 ml/min). The desired fractions were combined and the solvents evaporated under reduced pressure to yield 2.1 g (91% recovery) of the title compound as a colorless liquid. vigorously stirred for 1 hr The layers were separated the organic layer was washed twice with 200 ml portions of water dried (magnesium sulfate) the solvent evaporated under reduced pressure