4-Hydroxybenzaldehyde → 4-(6-Hydroxyhexoxy)benzaldehyde

To a solution of 40 g (1 mole) of sodium hydroxide in 60 ml of water and 400 ml of ethanol were added 122.12 g (1 mole) of 4-hydroxybenzaldehyde, 30 g of sodium iodide and 136.62 g (1 mole) of 1-chloro-6-hydroxyhexane. The mixture was heated at reflux for 24 hours under a nitrogen atmosphere. After cooling, the mixture was filtered and the solvent was removed under reduced pressure. Water (400 ml) was added to the residue and the mixture was extracted twice with 400 ml of ethyl acetate. The ethyl acetate layers were extracted twice with 200 ml of 5% aq. sodium hydroxide, and once with 200 ml of brine, dried over magnesium sulfate, and the solvent was evaporated. A brown oil (202 g, 91%) was obtained, which crystallized slowly.

1. temperatureThe mixture was heated
2. temperatureat reflux for 24 hours under a nitrogen atmosphere
3. temperatureAfter cooling
4. filtrationthe mixture was filtered
5. customthe solvent was removed under reduced pressure
6. additionWater (400 ml) was added to the residue
7. extractionthe mixture was extracted twice with 400 ml of ethyl acetate
8. extractionThe ethyl acetate layers were extracted twice with 200 ml of 5% aq. sodium hydroxide
9. dry with materialonce with 200 ml of brine, dried over magnesium sulfate
10. customthe solvent was evaporated

ORD record

ord-c9c9bdf946be4a7fb3eab5016f1e6009

Source dataset

uspto-grants-2007_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07311948B2