Resorcinol → 3-(propan-2-yloxy)phenol

To a solution of 1,3-benzenediol (8 g, 72.7 mmol) and 2-iodopropane (12 g, 70.6 mmol) in ethanol (100 mL preheated at reflux) was added a solution of KOH (83%, 5.3 g, 77.6 mmol) in water (20 mL) over a period of 30 minutes. The mixture was refluxed for 3 hours and poured into NaOH (1 N, 100 mL). The resulting mixture was extracted with ethyl acetate (3 times 50 mL) and the aqueous layer was acidified with 10% HCl to adjust the pH=5 and extracted with ethyl acetate (3 times 50 mL). The combined extracts were washed with brine (50 mL), dried and concentrated under vacuum. The residue was purified by column chromatography on silica gel (PE:EtOAc=5:1) to afford the title compound as a colourless oil (2.1 g).

1. temperatureThe mixture was refluxed for 3 hours
2. extractionThe resulting mixture was extracted with ethyl acetate (3 times 50 mL)
3. extractionextracted with ethyl acetate (3 times 50 mL)
4. washThe combined extracts were washed with brine (50 mL)
5. customdried
6. concentrationconcentrated under vacuum
7. customThe residue was purified by column chromatography on silica gel (PE:EtOAc=5:1)

ORD record

ord-82aedcf163014c44af5dfd11acf5dda4

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722695B2