Ferulic Acid → Methyl 3-(4-hydroxy-3-methoxyphenyl)propanoate

20 ml of 10% hydrogen chloride-methanol was added to 1.94 g (10 mmol) of ferulic acid and the mixture was stirred at room temperature for one day. After the reaction mixture was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, washed twice with water, and dried (MgSO4). The solvent was distilled off. The resulting residue was dissolved in 25 ml of methanol. 0.5 g of 10% palladium-carbon was added thereto and the solution was stirred overnight under hydrogen atmosphere. The reaction mixture was filtered and the filtrate was concentrated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1 (v/v)) to obtain 1.86 g (8.85 mmol) of methyl 3-(4-hydroxy-3-methoxyphenyl)propionate as a colorless oily substance. Its spectroscopic data are as follows:

1. concentrationAfter the reaction mixture was concentrated under reduced pressure
2. dissolutionthe residue was dissolved in ethyl acetate
3. washwashed twice with water
4. dry with materialdried (MgSO4)
5. distillationThe solvent was distilled off
6. dissolutionThe resulting residue was dissolved in 25 ml of methanol
7. addition0.5 g of 10% palladium-carbon was added
8. stirringthe solution was stirred overnight under hydrogen atmosphere
9. filtrationThe reaction mixture was filtered
10. concentrationthe filtrate was concentrated
11. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1 (v/v))

ORD-Eintrag

ord-f3390c931c9246f8960c4609f93d11c4

Quelldatensatz

uspto-grants-2000_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06069149