7-hydroxy-2,2-dimethyl-3H-chromen-4-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: Following the procedure of Example 30 but using 7-hydroxy-2,2-dimethyl-4-chromanone and 1-(2-hydroxyethyl)imidazole, there was obtained the title compound as a solid, mp 84-86° C. The structure was confirmed by NMR and mass spectroscopy. MS m/z 287 (M+H+).

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

Procedure: 3-Bromobenzotrifluoride (61 g) in dry ether (100 ml) was added to magnesium (6.6 g) in ether (50 ml). 2,2-Dimethylchroman-4-one-7-ol (17.4 g) suspended in ether (500 ml) was added and the mixture refluxed for 16 hourss. The reaction mixture was poured into ammonium chloride solution and extracted with ether. The combined ether layers were washed with 2 N HCl (2×100 ml) and dried (MgSO4). Removal of the solvent under reduced pressure gave the title compound (25 g), m.p. 102°-106° C. was added the mixture refluxed for 16 hourss extracted with ether The combined ether layers were washed with 2 N HCl (2×100 ml) dried (MgSO4) Removal of the solvent under reduced pressure

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

Procedure: 3-Bromobenzotrifluoride (61 g) in dry ether (100 ml) was added to magnesium (6.6 g) in ether (50 ml). 2,2-Dimethylchroman-4-one-7-ol (17.4 g) suspended in ether (500 ml) was added and the mixture refluxed for 16 hourss. The reaction mixture was poured into ammonium chloride solution and extracted with ether. The combined ether layers were washed with 2 N HCl (2×100 ml) and dried (MgSO4). Removal of the solvent under reduced pressure gave the title compound (25 g), m.p. 102°-106° C. was added the mixture refluxed for 16 hourss extracted with ether The combined ether layers were washed with 2 N HCl (2×100 ml) dried (MgSO4) Removal of the solvent under reduced pressure

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

Procedure: Bromobenzene (141.3 g) in dry tethydrofuran (300 ml) was added to magnesium (23.7 g) in dry tetrahydrofuran (100 ml). 2,2-Dimethylchroman-4-one-7-ol (34.5 g) in dry tetrahydrofuran (250 ml) was then added and the solution refluxed for 48 hours. The mixture was poured into ammonium chloride solution, the tetrahydrofuran layer was separated and evaporated under reduced pressure. The aqueous layer was extracted with ethyl acetate and the organic layer and the residue from the tetrahydrofuran layer was shaken with 10% sodium hydroxide solution. The basic layer was acidified and re-extracted with ethyl acetate. The organic layers were dried (MgSO4). Removal of the solvent under reduced pressure gave an oil (26 g) which was chromatographed on silica. Elution with ether-petrol (1:1) gave the title compound (14 g). the solution refluxed for 48 hours the tetrahydrofuran layer was separated evaporated under reduced pressure The aqueous layer was extracted with ethyl acetate re-extracted with ethyl acetate The organic layers were dried (MgSO4) Removal of the solvent under reduced pressure

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

Procedure: Bromobenzene (141.3 g) in dry tethydrofuran (300 ml) was added to magnesium (23.7 g) in dry tetrahydrofuran (100 ml). 2,2-Dimethylchroman-4-one-7-ol (34.5 g) in dry tetrahydrofuran (250 ml) was then added and the solution refluxed for 48 hours. The mixture was poured into ammonium chloride solution, the tetrahydrofuran layer was separated and evaporated under reduced pressure. The aqueous layer was extracted with ethyl acetate and the organic layer and the residue from the tetrahydrofuran layer was shaken with 10% sodium hydroxide solution. The basic layer was acidified and re-extracted with ethyl acetate. The organic layers were dried (MgSO4). Removal of the solvent under reduced pressure gave an oil (26 g) which was chromatographed on silica. Elution with ether-petrol (1:1) gave the title compound (14 g). the solution refluxed for 48 hours the tetrahydrofuran layer was separated evaporated under reduced pressure The aqueous layer was extracted with ethyl acetate re-extracted with ethyl acetate The organic layers were dried (MgSO4) Removal of the solvent under reduced pressure

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

Procedure: In 100 ml of methyl-ethyl-ketone 3.8 g (20 millimoles) of 7-hydroxy-2,2-dimethyl-4-chromanone are dissolved, whereupon 8.3 g (60 millimoles) of potassium carbonate, 0.5 g potassium iodide and thereafter 4.6 g (25 millimoles) of morpholinyl-ethyl-chloride hydrochloride are added and the reaction mixture is heated to boiling for 10 hours. The reaction having been completed the reaction mixture is cooled, the inorganic salt filtered off, washed twice with 20 ml of acetone each and the solvent is removed. The residue is treated with 100 ml of water. Thus 5.2 g of the desired compound are obtained in the form of white crystals, yield 85.3%. Mp.: 61°-63° C. the reaction mixture is heated is cooled the inorganic salt filtered off washed twice with 20 ml of acetone each and the solvent is removed The residue is treated with 100 ml of water

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

Procedure: To a mixture of 40 ml of methanol, 5 ml of water 1.1 g (20 millimoles) of potassium hydroxide and 3.8 g (20 millimoles) of 7-hydroxy-2,2-dimethyl-4-chromanone under stirring 11.6 g (14 ml, 0.2 mole) of propene oxide are added and the reaction mixture is refluxed for 5 hours. The reaction mixture is diluted with 200 ml of water and worked up according to Example 12. Thus 4.0 g of the desired compound are obtained, yield 80%. Mp.: 111°-113° C. are added the reaction mixture is refluxed for 5 hours

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

Procedure: A mixture of 20 ml of a 10% sodium hydroxide solution, 40 ml of dichloromethane, 0.5 g (2 millimoles) of tetrabutyl-ammonium-hydrogensulfate and 10 millimoles of 7-hydroxy-2,2-dimethyl-4-chromanone is intensively stirred for 30 minutes. To the mixture 2.4 g (2.1 ml, 25 millimoles) of chloromethyl-thiomethyl-ether are added, the reaction mixture is stirred for 20 minutes at room temperature and worked up according to Example 12. Thus 2.0 g of the desired compound are obtained in the form of an orange oil, yield 79%. the reaction mixture is stirred for 20 minutes at room temperature