3-(3-Hydroxyphenyl)-2-propenoic acid → Methyl 3-(3-hydroxyphenyl)propionate

20 ml of 10% hydrogen chloride-methanol was added to 1.64 g (10 mmol) of 3-hydroxycinnamic acid and the mixture was stirred at room temperature for one day. 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 residue was dissolved in 25 ml of methanol, 0.5 g of 10% palladium-carbon was added and the mixture was stirred overnight under hydrogen atmosphere. The reaction mixture was filtered and the filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:1 (v/v)) to obtain 1.75 g (9.71 mmol) of methyl 3-(3-hydroxyphenyl)propionate as a colorless oily substance. Its spectroscopic data are as follows:

1. concentrationThe 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 residue was dissolved in 25 ml of methanol
7. addition0.5 g of 10% palladium-carbon was added
8. stirringthe mixture was stirred overnight under hydrogen atmosphere
9. filtrationThe reaction mixture was filtered
10. concentrationthe filtrate was concentrated
11. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:1 (v/v))

ORD record

ord-ebd6cb4795ff48b5bcf043e09a1b2aa9

Source dataset

uspto-grants-2000_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06069149