4-heptoxybenzaldehyde

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

Procedure: A suspension of sodium boron hydride (6.9 g) in isopropyl alcohol (500 ml) was dropwise added to a solution of p-heptyloxybenzaldehyde (119 g) in isopropyl alcohol (300 ml), followed by heating the mixture to 70° C. to form a uniform solution, which was then agitated at 70° C. for 3 hours and allowed to stand overnight, followed by adding 6N-HCl (100 ml) and water (200 ml), heating the mixture to 60° C., distilling off most of the solvent, extracting with toluene, washing with water, washing with alkali, washing with water to make it neutral, drying, concentrating and recrystallizing the residue from a mixed solvent of ethanol (200 ml) and water (60 ml) to obtain p-heptyloxybenzyl alcohol (74.9 g). This product (40 g) together with 47% aqueous hydrogen bromic acid (200 g) were agitated at 80° C. for 7 hours and allowed to stand overnight, followed by extracting with n-heptane (200 ml), washing the n-heptane layer with water till the washing water became neutral, drying, concentrating and subjecting the residue to vacuum distillation to obtain p-heptyloxybenzyl bromide (IIa-2) (28 g) having a b.p. of 174°-175° C./6 Torr. to form a uniform solution, which to stand overnight heating the mixture to 60° C. distilling off most of the solvent extracting with toluene washing with water washing with alkali, washing with water drying concentrating recrystallizing the residue from a mixed solvent of ethanol (200 ml) and water (60 ml)

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

Procedure: A suspension of sodium boron hydride (6.9 g) in isopropyl alcohol (500 ml) was dropwise added to a solution of p-heptyloxybenzaldehyde (119 g) in isopropyl alcohol (300 ml), followed by heating the mixture to 70° C. to form a uniform solution, which was then agitated at 70° C. for 3 hours and allowed to stand overnight, followed by adding 6N-HCl (100 ml) and water (200 ml), heating the mixture to 60° C., distilling off most of the solvent, extracting with toluene, washing with water, washing with alkali, washing with water to make it neutral, drying, concentrating and recrystallizing the residue from a mixed solvent of ethanol (200 ml) and water (60 ml) to obtain p-heptyloxybenzyl alcohol (74.9 g). This product (40 g) together with 47% aqueous hydrogen bromic acid (200 g) were agitated at 80° C. for 7 hours and allowed to stand overnight, followed by extracting with n-heptane (200 ml), washing the n-heptane layer with water till the washing water became neutral, drying, concentrating and subjecting the residue to vacuum distillation to obtain p-heptyloxybenzyl bromide (IIa-2) (28 g) having a b.p. of 174°-175° C./6 Torr. to form a uniform solution, which to stand overnight heating the mixture to 60° C. distilling off most of the solvent extracting with toluene washing with water washing with alkali, washing with water drying concentrating recrystallizing the residue from a mixed solvent of ethanol (200 ml) and water (60 ml)

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

Procedure: A suspention of sodium boron hydride (6.9 g) in isopropyl alcohol (500 ml) was dropwise added to a solution of p-heptyloxybenzaldehyde (119 g) in isopropyl alcohol (300 ml), followed by heating the mixture to 70° C. to form a uniform solution, which was then agitated at 70° C. for 3 hours and allowed to stand overnight, followed by adding 6N-HCl (100 ml) and water (200 ml), heating the mixture to 60° C., distilling off most of the solvent, extracting with toluene, washing with water, washing with alkali, washing with water to make it neutral, drying, concentrating and recrystallizing the residue from a mixed solvent of ethanol (200 ml) and water (60 ml) to obtain p-heptyloxybenzyl alcohol (74.9 g). This product (40 g) together with 47% aqueous hydrogen bromic acid (200 g) were agitated at 80° C. for 7 hours and allowed to stand overnight, followed by extracting with n-heptane (200 ml), washing the n-heptane layer with water till the washing water became neutral, drying, concentrating and subjecting the residue to vacuum distillation to obtain p-heptyloxybenzyl bromide (IIa-2) (28 g) having a b.p. of 174°-175° C./6 Torr. to form a uniform solution, which to stand overnight heating the mixture to 60° C. distilling off most of the solvent extracting with toluene washing with water washing with alkali, washing with water drying concentrating recrystallizing the residue from a mixed solvent of ethanol (200 ml) and water (60 ml)

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

Procedure: A suspention of sodium boron hydride (6.9 g) in isopropyl alcohol (500 ml) was dropwise added to a solution of p-heptyloxybenzaldehyde (119 g) in isopropyl alcohol (300 ml), followed by heating the mixture to 70° C. to form a uniform solution, which was then agitated at 70° C. for 3 hours and allowed to stand overnight, followed by adding 6N-HCl (100 ml) and water (200 ml), heating the mixture to 60° C., distilling off most of the solvent, extracting with toluene, washing with water, washing with alkali, washing with water to make it neutral, drying, concentrating and recrystallizing the residue from a mixed solvent of ethanol (200 ml) and water (60 ml) to obtain p-heptyloxybenzyl alcohol (74.9 g). This product (40 g) together with 47% aqueous hydrogen bromic acid (200 g) were agitated at 80° C. for 7 hours and allowed to stand overnight, followed by extracting with n-heptane (200 ml), washing the n-heptane layer with water till the washing water became neutral, drying, concentrating and subjecting the residue to vacuum distillation to obtain p-heptyloxybenzyl bromide (IIa-2) (28 g) having a b.p. of 174°-175° C./6 Torr. to form a uniform solution, which to stand overnight heating the mixture to 60° C. distilling off most of the solvent extracting with toluene washing with water washing with alkali, washing with water drying concentrating recrystallizing the residue from a mixed solvent of ethanol (200 ml) and water (60 ml)

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

Procedure: General procedure K was used to convert 4-hydroxybenzaldehyde (8.2 mmols) and 1-bromoheptane (12.3 mmols) to 6.6 mmols (80%) of the title product was recovered. 1H NMR (300 MHz, CDCl3) δ 9.87 (s, 1H), 7.82 (d, J=8.8 Hz, 2H), 6.99 (d, J=8.7 Hz, 2H), 4.03 (t, J=6.5 Hz, 2H), 1.81 (quin., J=6 Hz, 1H), 1.24-1.53 (m, 8H), 0.89 (t, J=6.8 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 191.0, 164.4, 132.13, 129.8, 114.9, 68.6, 31.9, 29.18, 29.1, 26.1, 22.7, 14.2.

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

Procedure: Anhydrous potassium carbonate (55.5 g, 0.4 mol) was added to a stirred solution of 4-hydroxybenzaldehyde (24.5 g, 0.2 mol) in acetone (300 cm3), over a period of 30 min at room temperature. 1-Bromoheptane (40.3 g, 0.225 mol) was added dropwise and the resulting mixture heated under reflux (12 h). The solution was poured into water (1000 cm3), the product extracted into diethyl ether (2×300 cm3), and the combined ethereal extracts dried (MgSO4). The solvent was removed in vacuo and the product isolated as a colourless oil by distillation under reduced pressure. the resulting mixture heated under reflux (12 h) the product extracted into diethyl ether (2×300 cm3) the combined ethereal extracts dried (MgSO4) The solvent was removed in vacuo the product isolated as a colourless oil by distillation under reduced pressure

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

Procedure: A suspension of sodium boron hydride (6.9 g) in isopropyl alcohol (500 ml) was dropwise added to a solution of p-heptyloxybenzaldehyde (119 g) in isopropyl alcohol (300 ml), followed by heating the mixture to 70° C. to form a uniform solution, which was then agitated at 70° C. for 3 hours and allowed to stand overnight, followed by adding 6N-HCl (100 ml) and water (200 ml), heating the mixture to 60° C., distilling off most of the solvent, extracting with toluene, washing with water, washing with alkali, washing with water to make it neutral, drying, concentrating and recrystallizing the residue from a mixed solvent of ethanol (200 ml) and water (60 ml) to obtain p-heptyloxybenzyl alcohol (74.9 g). This product (40 g) together with 47% aqueous hydrogen bromic acid (200 g) were agitated at 80° C. for 7 hours and allowed to stand overnight, followed by extracting with n-heptane (200 ml), washing the n-heptane layer with water till the washing water became neutral, drying, concentrating and subjecting the residue to vacuum distillation to obtain p-heptyloxybenzyl bromide (IIa-2) (28 g) having a b.p. of 174°-175° C./6 Torr. to form a uniform solution, which to stand overnight heating the mixture to 60° C. distilling off most of the solvent extracting with toluene washing with water washing with alkali, washing with water drying concentrating recrystallizing the residue from a mixed solvent of ethanol (200 ml) and water (60 ml)

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

Procedure: A suspention of sodium boron hydride (6.9 g) in isopropyl alcohol (500 ml) was dropwise added to a solution of p-heptyloxybenzaldehyde (119 g) in isopropyl alcohol (300 ml), followed by heating the mixture to 70° C. to form a uniform solution, which was then agitated at 70° C. for 3 hours and allowed to stand overnight, followed by adding 6N-HCl (100 ml) and water (200 ml), heating the mixture to 60° C., distilling off most of the solvent, extracting with toluene, washing with water, washing with alkali, washing with water to make it neutral, drying, concentrating and recrystallizing the residue from a mixed solvent of ethanol (200 ml) and water (60 ml) to obtain p-heptyloxybenzyl alcohol (74.9 g). This product (40 g) together with 47% aqueous hydrogen bromic acid (200 g) were agitated at 80° C. for 7 hours and allowed to stand overnight, followed by extracting with n-heptane (200 ml), washing the n-heptane layer with water till the washing water became neutral, drying, concentrating and subjecting the residue to vacuum distillation to obtain p-heptyloxybenzyl bromide (IIa-2) (28 g) having a b.p. of 174°-175° C./6 Torr. to form a uniform solution, which to stand overnight heating the mixture to 60° C. distilling off most of the solvent extracting with toluene washing with water washing with alkali, washing with water drying concentrating recrystallizing the residue from a mixed solvent of ethanol (200 ml) and water (60 ml)