Potassium Carbonate → HCID 69433926, compound

Temperature

85 °C

A solution of 5.89 g (27 mmol) of 1-bromo-4-hydroxy-3-methoxy-5-methylbenzene (Syn. Lett. 1997, 1351-1352) in 100 mL of acetonitrile was treated with 5.33 g (38.5 mmol) of powdered K2CO3 and 5.75 mL (31.8 mmol) of 1-iodooctane. After stirring at 85° C. for 19 h, the reaction was cooled and concentrated. The residue was dissolved in 100 mL of H2O and extracted with 100 mL of Et2O. After separating phases, the organic layer was washed with 100 mL of 10% Na2S2O3, dried over MgSO4 and concentrated. The residue was purified on a Biotage 40L column using a gradient of hexane, 99/1 v/v hexane/EtOAc and 98/2 v/v hexane/EtOAc to afford 0.43 g of the title compound as a colorless oil. Several mixed column fractions were rechromatographed to yield an additional 703 mg of the title compound. RF: 0.63 (19/1 v/v hexane/EtOAc); 1H-NMR (500 MHz) δ 0.93 (t, J=6.8, 3H), 1.33-1.39 (m, 8H), 1.46-1.52 (m, 2H), 1.75-1.81 (m, 2H), 2.27 (s, 3H), 3.85 (s, 3H), 3.91 (t, J=6.6, 2H), 6.90 (d, J=2.3, 11H), 6.95 (d, J=2.3, 11H).

1. temperaturethe reaction was cooled
2. concentrationconcentrated
3. dissolutionThe residue was dissolved in 100 mL of H2O
4. extractionextracted with 100 mL of Et2O
5. customAfter separating phases
6. washthe organic layer was washed with 100 mL of 10% Na2S2O3
7. dry with materialdried over MgSO4
8. concentrationconcentrated
9. customThe residue was purified on a Biotage 40L column

ORD record

ord-e33b4c9b7a2f4c46bd95a5c699707dea

Source dataset

uspto-grants-2007_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07309721B2