Hydrochloric Acid → 4-Heptyloxybenzyl alcohol

Temperature

70 °C

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.

1. customto form a uniform solution, which
2. waitto stand overnight
3. temperatureheating the mixture to 60° C.
4. distillationdistilling off most of the solvent
5. extractionextracting with toluene
6. washwashing with water
7. washwashing with alkali,
8. washwashing with water
9. customdrying
10. concentrationconcentrating
11. customrecrystallizing the residue from a mixed solvent of ethanol (200 ml) and water (60 ml)

ORD record

ord-f1ad1187ebd84cb4bdcc06cdc752e464

Source dataset

uspto-grants-1988_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04751019