2-Propoxyphenol

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

Procedure: To 15 ml. of dioxane are added 3 g. of ortho-normalpropoxyphenol, 9 ml. of 37% of formalin and 2.4 g. of phenethylamine. The mixture is heated on reflux for 3 hours and distilled to remove the solvent under reduced pressure. The residue is purified by column chromatography on silica gel with a mixture of acetone and benzene (1:4). The resultant oily substance is cooled to be crystallized. A small portion of ethanol is added to the crystals, followed by filtration. The procedure yields 3-phenethyl-8-normal-propoxy-3,4-dihydro-2H-1,3-benzoxazine as colorless needless melting at 84° C. Yield: 3.8 g. The mixture is heated on reflux for 3 hours distilled to remove the solvent under reduced pressure The residue is purified by column chromatography on silica gel with a mixture of acetone and benzene (1:4) The resultant oily substance is cooled to be crystallized A small portion of ethanol is added to the crystals followed by filtration

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

Procedure: To 15 ml. of dioxane are added 3 g. of ortho-normalpropoxyphenol, 9 ml. of 37% of formalin and 2.4 g. of phenethylamine. The mixture is heated on reflux for 3 hours and distilled to remove the solvent under reduced pressure. The residue is purified by column chromatography on silica gel with a mixture of acetone and benzene (1:4). The resultant oily substance is cooled to be crystallized. A small portion of ethanol is added to the crystals, followed by filtration. The procedure yields 3-phenethyl-8-normal-propoxy-3,4-dihydro-2H-1,3-benzoxazine as colorless needless melting at 84° C. Yield: 3.8 g. The mixture is heated on reflux for 3 hours distilled to remove the solvent under reduced pressure The residue is purified by column chromatography on silica gel with a mixture of acetone and benzene (1:4) The resultant oily substance is cooled to be crystallized A small portion of ethanol is added to the crystals followed by filtration

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

Procedure: The compound was prepared as described in Example 1, using sodium (3.45 g; 150 mole), 0-propoxyphenol (11.4 g; 75 mmole) and diisopropylaminoethylchloride hydrochloride (15.0 g; 75 mmole) in 200 ml of ethanol. Yield 12.7 g (64%) of product, boiling at 109°-110° C under a pressure of 0.001 mm.Hg, nD25 : 1.4961. Calcd. for C17H29NO2 : C 73.07%, H 10.46%, N 5.01%. Found C 73.2% H 10.5%, N 4.96%. The compound was prepared

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

Procedure: The compound was prepared as described in Example 1, using sodium (3.45 g; 150 mole), 0-propoxyphenol (11.4 g; 75 mmole) and diisopropylaminoethylchloride hydrochloride (15.0 g; 75 mmole) in 200 ml of ethanol. Yield 12.7 g (64%) of product, boiling at 109°-110° C under a pressure of 0.001 mm.Hg, nD25 : 1.4961. Calcd. for C17H29NO2 : C 73.07%, H 10.46%, N 5.01%. Found C 73.2% H 10.5%, N 4.96%. The compound was prepared

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

Procedure: To 15 ml. of dioxane are added 3 g. of ortho-normalpropoxyphenol, 9 ml. of 37% of formalin and 2.4 g. of phenethylamine. The mixture is heated on reflux for 3 hours and distilled to remove the solvent under reduced pressure. The residue is purified by column chromatography on silica gel with a mixture of acetone and benzene (1:4). The resultant oily substance is cooled to be crystallized. A small portion of ethanol is added to the crystals, followed by filtration. The procedure yields 3-phenethyl-8-normal-propoxy-3,4-dihydro-2H-1,3-benzoxazine as colorless needless melting at 84° C. Yield: 3.8 g. The mixture is heated on reflux for 3 hours distilled to remove the solvent under reduced pressure The residue is purified by column chromatography on silica gel with a mixture of acetone and benzene (1:4) The resultant oily substance is cooled to be crystallized A small portion of ethanol is added to the crystals followed by filtration

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

Procedure: The compound was prepared as described in Example 1, using sodium (3.45 g; 150 mole), 0-propoxyphenol (11.4 g; 75 mmole) and diisopropylaminoethylchloride hydrochloride (15.0 g; 75 mmole) in 200 ml of ethanol. Yield 12.7 g (64%) of product, boiling at 109°-110° C under a pressure of 0.001 mm.Hg, nD25 : 1.4961. Calcd. for C17H29NO2 : C 73.07%, H 10.46%, N 5.01%. Found C 73.2% H 10.5%, N 4.96%. The compound was prepared

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

Procedure: To 15 ml. of dioxane are added 3 g. of ortho-normalpropoxyphenol, 9 ml. of 37% of formalin and 2.4 g. of phenethylamine. The mixture is heated on reflux for 3 hours and distilled to remove the solvent under reduced pressure. The residue is purified by column chromatography on silica gel with a mixture of acetone and benzene (1:4). The resultant oily substance is cooled to be crystallized. A small portion of ethanol is added to the crystals, followed by filtration. The procedure yields 3-phenethyl-8-normal-propoxy-3,4-dihydro-2H-1,3-benzoxazine as colorless needless melting at 84° C. Yield: 3.8 g. The mixture is heated on reflux for 3 hours distilled to remove the solvent under reduced pressure The residue is purified by column chromatography on silica gel with a mixture of acetone and benzene (1:4) The resultant oily substance is cooled to be crystallized A small portion of ethanol is added to the crystals followed by filtration