4-hexoxybenzaldehyde

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: A solution of 4-hexyloxybenzaldehyde (3.83 g, 18.6 mmol) in 120 mL of benzene was refluxed with N-tert-butylhydroxylamine (3.32 g, 37.2 mmol) for 18 hours. The reaction mixture was then concentrated by rotary evaporation and the resulting residue was purified by silica gel column chromatography using 50:50 ethyl acetate/hexane to afford the title compound (2.88 g, 55.8 % yield) as a solid, m.p. 69.0° C. The reaction mixture was then concentrated by rotary evaporation the resulting residue was purified by silica gel column chromatography

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

Procedure: A solution of 4-hexyloxybenzaldehyde (3.83 g, 18.6 mmol) in 120 mL of benzene was refluxed with N-tert-butylhydroxylamine (3.32 g, 37.2 mmol) for 18 hours. The reaction mixture was then concentrated by rotary evaporation and the resulting residue was purified by silica gel column chromatography using 50:50 ethyl acetate/hexane to afford the title compound (2.88 g, 55.8 % yield) as a solid, m.p. 69.0° C. The reaction mixture was then concentrated by rotary evaporation the resulting residue was purified by silica gel column chromatography

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

Procedure: 49.2 g of 3-(4-methoxyphenyl)-2-propanone and 61.8 g of 4-hexyloxybenzaldehyde were added to 100 ml of toluene containing 4 ml of piperidine. The resultant mixture was heated at reflux temperature overnight after which the solvent was removed in vacuo to afford the desired subtitled intermediate (46% yield), b.p. 230°-235° C. at reflux temperature overnight after which the solvent was removed in vacuo

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

Procedure: To a stirring solution of 20.6 g of 4-hexyloxybenzaldehyde and 11.8 g of 3-pyridylacetonitrile in methanol was added 25 ml of aqueous potassium hydroxide (25 percent). A precipitate formed and the resultant mixture was stirred at room temperature for an additional two hours. The resultant precipitate was collected by filtration, washed with water and recrystallized from ethanol to yield the intermediate, α-[[4-(hexyloxy)phenyl]methylene]-3-pyridylacetonitrile (m.p. 67°-68° C). 46 g of said nitrile, 10 g of Raney nickel, 150 ml of anhydrous ammonia and 300 ml of tetrahydrofuran were stirred at 100° C. for ten hours at a pressure of 1500 psi. The catalyst and solvent were removed and the residue was taken up in diethyl ether and fitered through magnesia-silica gel. The hydrochloride salt was made in the filtrate by the addition of anhydrous hydrochloric acid. Recrystallization from ethanol yielded β-[[4-(hexyloxy)phenyl]methyl]-3-pyridineethanamine dihydrochloride. A precipitate formed The resultant precipitate was collected by filtration washed with water recrystallized from ethanol

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

Procedure: A solution of 51.5 g of 4-hexyloxybenzaldehyde and 33.8 g of 4-fluorophenylacetonitrile in methanol was stirred at room temperature and aqueous sodium hydroxide (50 percent) was added dropwise until a precipitate appeared. Water was then added and the solids were collected by filtration to render α-[[4-(hexyloxy)phenyl]methylene]-4-fluorophenylacetonitrile which was reduced as follows. 40.2 g of said nitrile, 10 g of Raney nickel, 150 ml of anhydrous ammonia and 300 ml of tetrahydrofuran were stirred at 110° for 12 hours at a pressure of 2000 psi. The catalyst and solvent were removed and the hydrochloride salt was made in the filtrate by the addition of anhydrous hydrochloric acid. Recrystallization from methanol rendered the title compound (20 percent yield). the solids were collected by filtration The catalyst and solvent were removed the hydrochloride salt was made in the filtrate by the addition of anhydrous hydrochloric acid Recrystallization from methanol

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

Procedure: A solution of 51.5 g of 4-hexyloxybenzaldehyde and 33.8 g of 4-fluorophenylacetonitrile in methanol was stirred at room temperature and aqueous sodium hydroxide (50 percent) was added dropwise until a precipitate appeared. Water was then added and the solids were collected by filtration to render α-[[4-(hexyloxy)phenyl]methylene]-4-fluorophenylacetonitrile which was reduced as follows. 40.2 g of said nitrile, 10 g of Raney nickel, 150 ml of anhydrous ammonia and 300 ml of tetrahydrofuran were stirred at 110° for 12 hours at a pressure of 2000 psi. The catalyst and solvent were removed and the hydrochloride salt was made in the filtrate by the addition of anhydrous hydrochloric acid. Recrystallization from methanol rendered the title compound (20 percent yield). the solids were collected by filtration The catalyst and solvent were removed the hydrochloride salt was made in the filtrate by the addition of anhydrous hydrochloric acid Recrystallization from methanol

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

Procedure: Cyclohexanone (2.6 ml, 0.025 mol) was dissolved in ethanol (5 ml), and was added to sodium hydroxide (0.38 g, 0.01 mol) dissolved in water (6 ml) and ethanol (2 ml) and was left to stir for 20 min. 4-Hexyloxybenzaldehyde (10 ml, 0.048 mol), dissolved in ethanol (40 ml), was added and the mixture was stirred at room temperature for 16 h. A yellow crystalline solid was isolated by vacuum filtration and was washed with cold ethanol and dried in a vacuum oven. Yield=4.32 g, 36%. 1H NMR and 13C NMR showed expected signals. was added the mixture was stirred at room temperature for 16 h A yellow crystalline solid was isolated by vacuum filtration was washed with cold ethanol dried in a vacuum oven

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

Procedure: Cyclohexanone (2.6 ml, 0.025 mol) was dissolved in ethanol (5 ml), and was added to sodium hydroxide (0.38 g, 0.01 mol) dissolved in water (6 ml) and ethanol (2 ml) and was left to stir for 20 min. 4-Hexyloxybenzaldehyde (10 ml, 0.048 mol), dissolved in ethanol (40 ml), was added and the mixture was stirred at room temperature for 16 h. A yellow crystalline solid was isolated by vacuum filtration and was washed with cold ethanol and dried in a vacuum oven. Yield=4.32 g, 36%. 1H NMR and 13C NMR showed expected signals. was added the mixture was stirred at room temperature for 16 h A yellow crystalline solid was isolated by vacuum filtration was washed with cold ethanol dried in a vacuum oven

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

Procedure: 1-Indanone (4.17 g, 0.032 mol) was dissolved in ethanol (20 ml), and was added to sodium hydroxide (0.44 g, 0.011 mol) dissolved in water (8 ml) and ethanol (3 ml) and was left to stir for 20 min. 4-(Hexyloxy)benzaldehyde (6.4 ml, 0.031 mol), dissolved in ethanol (35 ml), was added to the mixture and was stirred for 4 hours. The product was isolated by vacuum filtration and was washed with cold ethanol (2×20 ml) and was dried in a vacuum oven. Yield=8.47 g, 85%. 1H NMR and 13C NMR gave expected signals. was added to the mixture was stirred for 4 hours The product was isolated by vacuum filtration was washed with cold ethanol (2×20 ml) was dried in a vacuum oven 1H NMR and 13C NMR gave expected signals