4-(4-hydroxyphenyl)butan-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:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared as described in General Method 5 using 10 g (60.9 mmol) of 4-(4-hydroxyphenyl)-2-butanone, 10.1 g (67 mmol) of tert-butyldimethyl silyl chloride, 4.56 g (67 mmol) of imidazole and 150 mL of DMF. The crude product was carried on "as is" to the next step (see Example KK).

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

Procedure: p-Hydroxy benzylacetone (1.5 g.), KOH (6 g.) and allyl bromide (1.2 g.) were stirred in ethanol (50 ml) overnight. Water was added and the mixture extracted with ether, which was evaporated to give the compound (1.6 g.) as an oil purified by column chromatography. the mixture extracted with ether, which was evaporated to give the compound (1.6 g.) as an oil purified by column chromatography

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

Procedure: p-Hydroxy benzylacetone (1.5 g.), KOH (6 g.) and allyl bromide (1.2 g.) were stirred in ethanol (50 ml) overnight. Water was added and the mixture extracted with ether, which was evaporated to give the compound (1.6 g.) as an oil purified by column chromatography. the mixture extracted with ether, which was evaporated to give the compound (1.6 g.) as an oil purified by column chromatography

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

Procedure: 5 mmol of 3-(1-triphenylmethyl-1H-imidazol-4-yl)propanol, 6 mmol of triphenylphosphine and 5 mmol of 4-(4-hydroxyphenyl)-2-butanone are dissolved under nitrogen in the cold. 6 mmol of diethyl azodicarboxylate, dissolved in 4 ml of THF, are added and the reaction mixture is stirred at room temperature for 48 hours. After evacuation of the solvent under reduced pressure and column chromatography (eluent: ethyl acetate), the residue is dissolved in 10 ml THF and 30 ml of 2N HCl and heated to 70° C. for 2 hours. The solvent is evaporated off under reduced pressure and triphenylmethanol is extracted using diethyl ether. The aqueous phase is neutralized with potassium carbonate and the product extracted with diethyl ether. The ethereal solution is dried and evaporated to obtain an oil, which is crystallized as hydrogen maleate from diethyl ether and ethanol. are added The solvent is evaporated off under reduced pressure and triphenylmethanol is extracted the product extracted with diethyl ether The ethereal solution is dried evaporated to obtain an oil, which is crystallized as hydrogen maleate from diethyl ether and ethanol

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

Procedure: The title compound was prepared as described in General Method 5 using 10 g (60.9 mmol) of 4-(4-hydroxyphenyl)-2-butanone, 10.1 g (67 mmol) of tert-butyldimethyl silyl chloride, 4.56 g (67 mmol) of imidazole and 150 mL of DMF. The crude product was carried on "as is" to the next step (see Example KK).

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

Procedure: A mixture of 4-[4-hydroxyphenyl]butan-2-one (16.4 g], 2-bromoethanol (16.9 g), sodium hydroxide (7.5 g), sodium iodide (7.5 g) and water (200 ml) was heated under reflux for 4 hours, cooled and extracted with dichloromethane. The extract was washed with brine, dried (MgSO4) and evaporated to dryness. The residual oil was distilled to give the title compound as a colourless liquid, bp 170°-1°/0.8 mm. P τ(CDCl3) 7.85 (3H, s), 7.15-7.35 (4H, complex), 7.4-7.6 (1H, t), 5.85-6.25 (4H, complex), 2.8-3.4 (4H, dd). was heated under reflux for 4 hours cooled extracted with dichloromethane The extract was washed with brine dried (MgSO4) evaporated to dryness The residual oil was distilled

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

Procedure: A solution of 4-(4-hydroxyphenyl)-2-butanone (100 g) in 500 ml of ethanol with anhydrous dimethylamine (300 ml) and 5% palladium on sulfide carbon (100 g) was placed in a high pressure reaction vessel and kept under 1000 psi of H2 at 175° C. for 8 hours. The resultant solution was then filtered and the solvent removed in vacuo to give an oil which was dissolved in 1N hydrochloric acid (100 ml) and extracted with two 100 ml portions of ether. The aqueous layer was adjusted to pH7 with 2N sodium hydroxide and extracted with an additional two 100 ml volumes of ether. The organic extract was retained and dried and reduced in volume to give 55 g (47% yield) of the desired subtitled intermediate. The resultant solution was then filtered the solvent removed in vacuo to give an oil which extracted with two 100 ml portions of ether extracted with an additional two 100 ml volumes of ether The organic extract dried

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

Procedure: 4-(4-Hydroxyphenyl)-2-butanone (49 g) was added by portions while warming to a stirred solution of potassium hydroxide (0.33 m) in 15 ml of water. To this was added dropwise, 49.8 g of 1-bromopentane and the resultant mixture was stirred at reflux temperature overnight. The mixture was allowed to cool after which 500 ml of 20% sodium hydroxide was added and the resultant mixture was stirred an additional 30 minutes followed by extraction with ethylacetate. The organic extracts were dried and evaporated to yield approximately 63 g of the desired 4-(4-pentoxyphenyl)-2-butanone which was used to prepare the title compound as follows. To this was added dropwise at reflux temperature overnight was added followed by extraction with ethylacetate The organic extracts were dried evaporated

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of benzyltriphenylphosphonium bromide (10.9 g, 25.1 mmol, 1.2 equiv.) in THF (35 mL), was added potassium-t-amylat (1.7 M in toluene, 20 mL, 34.0 mmol, 1.7 equiv.) at 25° C. 4-(4-Hydroxyphenyl)butan-2-one (3.3 g, 20.1 mmol, 1.0 equiv.) in THF (5 mL) was added to the red suspension, and the mixture was stirred at 70° C. for 30 min. After addition of 20% aq. AcOH-solution (10 mL) at 25° C., the aqueous layer was diluted with hexanes (50 mL). The organic phase was washed with H2O (2×30 mL) and MeOH/H2O (8:2, 2×20 mL) and concentrated. The residue was purified by flash chromatography on SiO2 to yield 2.10 g (44%) of the title compound as a white solid. The organic phase was washed with H2O (2×30 mL) and MeOH/H2O (8:2, 2×20 mL) concentrated The residue was purified by flash chromatography on SiO2