Hydrochloric Acid → 5-Benzyl-2-hydroxy-benzaldehyde

Temperature

75 °C

157 g of sodium hydroxide (50% in water) was added all at once to a stirred mixture of 100 g of p-benzylphenol in 165 ml of ethanol. The mixture was heated to 75°-80° C., and 161.5 g of chloroform was added drop-by-drop to the stirred mixture over a 5-hour period, at 75°-80° C., then was stirred for 2 hours at 75° C. Then 80.8 g of chloroform was added drop-by-drop, at 75°-80° C., and the mixture was stirred for 1 hour at 75° C. This procedure was repeated. The mixture was concentrated under reduced pressure to give a solid residue. The residue was poured into water, and the stirred mixture was acidified with concentrated hydrochloric acid. The aqueous phase was separated, extracted with ether and the extract was concentrated under reduced pressure to give an oil. The oil was extracted with petroleum ether. The extract was concentrated under reduced pressure. The residue was suspended in 150 ml of a saturated solution of sodium bisulfite and the mixture was stirred for 1 hour at room temperature. The liquid was decanted, and the solid was washed with water, stirred with ethanol and the mixture was filtered. The solid was washed with ether, then suspended in 10% sulfuric acid solution. The resulting mixture was stirred for 11/2 hours, then extracted with ether. The extract was dried (MgSO4) and concentrated under reduced pressure to give 5-benzylsalicylaldehyde (1A).

1. temperatureThe mixture was heated to 75°-80° C.
2. stirringthe mixture was stirred for 1 hour at 75° C
3. concentrationThe mixture was concentrated under reduced pressure
4. customto give a solid residue
5. customThe aqueous phase was separated
6. extractionextracted with ether
7. concentrationthe extract was concentrated under reduced pressure
8. customto give an oil
9. extractionThe oil was extracted with petroleum ether
10. concentrationThe extract was concentrated under reduced pressure
11. stirringthe mixture was stirred for 1 hour at room temperature
12. customThe liquid was decanted
13. washthe solid was washed with water
14. stirringstirred with ethanol
15. filtrationthe mixture was filtered
16. washThe solid was washed with ether
17. stirringThe resulting mixture was stirred for 11/2 hours
18. extractionextracted with ether
19. dry with materialThe extract was dried (MgSO4)
20. concentrationconcentrated under reduced pressure

ORD record

ord-2b500a1084364936b6316fdaa053a0b8

Source dataset

uspto-grants-1980_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04213999