Methyl iodide → [4-(2-Methoxyethoxy)phenyl]methanol

To a solution of 4-(2-methoxyethoxy)benzoic acid (100 mg, 0.51 mmol) in N,N-dimethylformamide (2 mL) were added potassium carbonate (282 mg, 2.04 mmol) and iodomethane (79 μL, 1.27 mmol) at room temperature. The mixture was stirred at the same temperature overnight, and then to the reaction solution was added water. The mixture was extracted with ethyl acetate twice. The organic layer was combined, washed with water and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was dissolved in tetrahydrofuran (3 mL), and then thereto was added lithium borohydride (53 mg, 2.45 mmol) at 0° C. The reaction solution was slowly warmed to room temperature, and stirred for 3 days. To the reaction solution was added water, and the mixture was extracted with ethyl acetate twice. The organic layer was combined, washed with water and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to give [4-(2-methoxyethoxy)phenyl]methanol (61 mg, 68%) as a colorless and clear oil.

1. extractionThe mixture was extracted with ethyl acetate twice
2. washwashed with water and saturated brine
3. dry with materialdried over anhydrous sodium sulfate
4. concentrationconcentrated under reduced pressure
5. dissolutionThe resulting residue was dissolved in tetrahydrofuran (3 mL)
6. stirringstirred for 3 days
7. extractionthe mixture was extracted with ethyl acetate twice
8. washwashed with water and saturated brine
9. dry with materialdried over anhydrous sodium sulfate
10. concentrationconcentrated under reduced pressure

ORD record

ord-13cbe3c0e7974beaa3c8308f772b6b6e

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987445B2