Hydrochloric Acid → 3-Methoxy-2-propylphenol

2-Propyl resorcinol (1.50 g, 9.86 mmol) was dissolved in DMF (anhydrous, 20 mL) and K2CO3 (681 mg, 4.93 mmol) was added. After stirring for 10 min at rt, iodomethane (0.92 mL, 14.8 mmol) was added and the reaction mixture was stirred for 6 h at 60° C. After cooling to rt, the reaction mixture was acidified with HCl (1 N aqueous solution) and concentrated under reduced pressure. Water was added and the aqueous phase was extracted with EtOAc (2×). The combined organic phases were dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification by silica gel flash chromatography (EtOAc/hexane (v/v) 1:15) gave 33 mg (24%) of the title compound as an oil. 1H NMR (400 MHz, CDCl3): δ 0.97 (t, 3H), 1.54 (m, 2H), 2.61 (t, 2H), 3.81 (s, 3H), 4.68 (br, 1H), 6.47 (m, 2H), 7.03 (t, 1H).

1. stirringthe reaction mixture was stirred for 6 h at 60° C
2. temperatureAfter cooling to rt
3. concentrationconcentrated under reduced pressure
4. additionWater was added
5. extractionthe aqueous phase was extracted with EtOAc (2×)
6. dry with materialThe combined organic phases were dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customPurification by silica gel flash chromatography (EtOAc/hexane (v/v) 1:15)

ORD record

ord-0f10f1ddcf8346ce8a00c044d7b981ec

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07906653B2