Hexane → (3-Ethoxy-4-methoxy-phenyl)-(4-methoxy-3-methyl-phenyl)-methanol

To a solution of 4-bromo-2-ethoxy-1-methoxy-benzene (1.7 g, 7.4 mmol) in THF (20 mL) was added a solution of n-butyllitium in hexane (2.8 mL, 2.5 N, 7.0 mmol) at −78° C. and kept for 20 min. To the mixture was added 4-methoxy-3-methyl-benzaldehyde (1.0 g, 90% pure, 6.0 mmol) at −78° C. After 18 h, water (30 mL) was added to the mixture, and the cold bath was removed. The mixture was stirred at room temperature for 20 min. The mixture was extracted with ethyl acetate (2×50 mL). The combined organic layers was washed with HCl (0.5 N, 50 mL), sodium hydrogen carbonate (50 mL, sat), brine (50 mL) and dried over magnesium sulfate. Removal of solvent gave (3-ethoxy-4-methoxy-phenyl)-(4-methoxy-3-methyl-phenyl)-methanol as a solid (2.0 g, 100% crude yield). The sample was used in the next step without further purification.

1. waitAfter 18 h
2. customthe cold bath was removed
3. extractionThe mixture was extracted with ethyl acetate (2×50 mL)
4. washThe combined organic layers was washed with HCl (0.5 N, 50 mL), sodium hydrogen carbonate (50 mL, sat), brine (50 mL)
5. dry with materialdried over magnesium sulfate
6. customRemoval of solvent

ORD record

ord-d3b74e1e0f7a4422b7c257bb8c3ef679

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07470723B2