2,4,4-trimethyl-5H-1,3-oxazole

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

Conditions: temp:220.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of phenol (33.2 g) and 2,4,4-trimethyloxazoline (18.1 g) was heated in a stirred pressure vessel at 220° C. for 48 hours. The oil obtained on cooling was dissolved in ethyl acetate, washed with 5M sodium hydroxide solution, water, brine, then dried and evaporated to give an oil which was distilled under high vacuum to give N-(1,1-dimethyl-2-phenoxyethyl)acetamide, b.p. 115-122° C. at 0.67 mbar. The oil obtained on cooling washed with 5M sodium hydroxide solution, water, brine dried evaporated to give an oil which was distilled under high vacuum

Conditions: temp:220.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of phenol (33.2 g) and 2,4,4-trimethyloxazoline (18.1 g) was heated in a stirred pressure vessel at 220° C. for 48 hours. The oil obtained on cooling was dissolved in ethyl acetate, washed with 5M sodium hydroxide solution, water, brine, then dried and evaporated to give an oil which was distilled under high vacuum to give N-(1,1-dimethyl-2-phenoxyethyl)acetamide, b.p. 115-122° C. at 0.67 mbar. The oil obtained on cooling washed with 5M sodium hydroxide solution, water, brine dried evaporated to give an oil which was distilled under high vacuum

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 226 g (2 mols) of 2,4,4-trimethyloxazoline were dropped at room temperature to 298 g (2 mols) 3-methyl-2-butenyl bromide in 400 ml absolute methylenchloride and were stirred for 12 hours at 20° C. After cooling to 0° C. 400 ml (2 mols) of a 30% solution of sodium methylate were added and the mixture was stirred for a further hour at room temperature. The solution was filtered and after removing off the solvent the residue was distilled. 368 g (1.72 mols, 86%) of 2-methoxy-3-(3-methyl-2-butenyl)-2,4,4-trimethyloxazolidine of boiling point 70°-76° C./0.05 mm Hg were obtained. NMR (CDCL3): α1.1 (s, 3H); 1.2 (s, 3H); 1.4 (s, 3H); 1.6-1.7 (bs, 6H); 3.2 (s, 3H); 3.25 (d, J=6.5 Hz, 2H); 3.65 (s, 2H); 5.25 (t, J=6.5 Hz, 1H). After cooling to 0° C the mixture was stirred for a further hour at room temperature The solution was filtered after removing off the solvent the residue was distilled

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 226 g (2 mols) of 2,4,4-trimethyloxazoline were dropped at room temperature to 298 g (2 mols) 3-methyl-2-butenyl bromide in 400 ml absolute methylenchloride and were stirred for 12 hours at 20° C. After cooling to 0° C. 400 ml (2 mols) of a 30% solution of sodium methylate were added and the mixture was stirred for a further hour at room temperature. The solution was filtered and after removing off the solvent the residue was distilled. 368 g (1.72 mols, 86%) of 2-methoxy-3-(3-methyl-2-butenyl)-2,4,4-trimethyloxazolidine of boiling point 70°-76° C./0.05 mm Hg were obtained. NMR (CDCL3): α1.1 (s, 3H); 1.2 (s, 3H); 1.4 (s, 3H); 1.6-1.7 (bs, 6H); 3.2 (s, 3H); 3.25 (d, J=6.5 Hz, 2H); 3.65 (s, 2H); 5.25 (t, J=6.5 Hz, 1H). After cooling to 0° C the mixture was stirred for a further hour at room temperature The solution was filtered after removing off the solvent the residue was distilled

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.3 g of a 40 percent strength NaHSO3 solution is added to a mixture of 9 g of 2-chloro-5-nitro-α-methylcinnamaldehyde and 10.4 g of 2,4,4-trimethyloxazoline in 50 ml of toluene, and the mixture is refluxed for 10 hours. It is evaporated down, and 10 ml of water and 10 ml of concentrated HCl are added to the crude product of the structure ##STR23## Heating at 100° C. for 7 hours results in cleavage of the oxazoline ring. The crude product is filtered off under suction, washed with water and dried. Yield: 7.1 g (66%), mp. 178°-185° C. the mixture is refluxed for 10 hours It is evaporated down 10 ml of water and 10 ml of concentrated HCl are added to the crude product of the structure results in cleavage of the oxazoline ring The crude product is filtered off under suction washed with water dried

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

Procedure: A mixture of 2-methoxy-5-nitrobenzaldehyde, 16 g, (U.S. Pat. No. 4,367,234), 2,4,4-trimethyl-2-oxazoline, 30 ml, (Aldrich Chemical Company), para toluenesulfornic acid, 0.5 g, in toluene, 100 ml, is refluxed overnight under a water separator. The mixture is evaporated, the residue dissolved in diethylether, 800 ml, and washed with water. The diethyl ether layer is separated, concentrated, and filtered to give 11.1 g of 4,5-dihydro-2-[2-(2-methoxy-5-nitrophenyl)ethenyl]-4,4-dimethyloxazole after recrystallization from diisopropyl ether; mp 115°-116° C. The mixture is evaporated the residue dissolved in diethylether 800 ml, and washed with water The diethyl ether layer is separated concentrated filtered

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

Procedure: A mixture of 2-methoxy-5-nitrobenzaldehyde, 16 g, (U.S. Pat. No. 4,367,234), 2,4,4-trimethyl-2-oxazoline, 30 ml, (Aldrich Chemical Company), para toluenesulfornic acid, 0.5 g, in toluene, 100 ml, is refluxed overnight under a water separator. The mixture is evaporated, the residue dissolved in diethylether, 800 ml, and washed with water. The diethyl ether layer is separated, concentrated, and filtered to give 11.1 g of 4,5-dihydro-2-[2-(2-methoxy-5-nitrophenyl)ethenyl]-4,4-dimethyloxazole after recrystallization from diisopropyl ether; mp 115°-116° C. The mixture is evaporated the residue dissolved in diethylether 800 ml, and washed with water The diethyl ether layer is separated concentrated filtered

Conditions: temp:220.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of phenol (33.2 g) and 2,4,4-trimethyloxazoline (18.1 g) was heated in a stirred pressure vessel at 220° C. for 48 hours. The oil obtained on cooling was dissolved in ethyl acetate, washed with 5M sodium hydroxide solution, water, brine, then dried and evaporated to give an oil which was distilled under high vacuum to give N-(1,1-dimethyl-2-phenoxyethyl)acetamide, b.p. 115-122° C. at 0.67 mbar. The oil obtained on cooling washed with 5M sodium hydroxide solution, water, brine dried evaporated to give an oil which was distilled under high vacuum

Conditions: temp:220.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of phenol (33.2 g) and 2,4,4-trimethyloxazoline (18.1 g) was heated in a stirred pressure vessel at 220° C. for 48 hours. The oil obtained on cooling was dissolved in ethyl acetate, washed with 5M sodium hydroxide solution, water, brine, then dried and evaporated to give an oil which was distilled under high vacuum to give N-(1,1-dimethyl-2-phenoxyethyl)acetamide, b.p. 115-122° C. at 0.67 mbar. The oil obtained on cooling washed with 5M sodium hydroxide solution, water, brine dried evaporated to give an oil which was distilled under high vacuum

Conditions: temp:220.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of phenol (33.2 g) and 2,4,4-trimethyloxazoline (18.1 g) was heated in a stirred pressure vessel at 220° C. for 48 hours. The oil obtained on cooling was dissolved in ethyl acetate, washed with 5M sodium hydroxide solution, water, brine, then dried and evaporated to give an oil which was distilled under high vacuum to give N-(1,1-dimethyl-2-phenoxyethyl)acetamide, b.p. 115-122° C. at 0.67 mbar. The oil obtained on cooling washed with 5M sodium hydroxide solution, water, brine dried evaporated to give an oil which was distilled under high vacuum

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