Methyl iodide → 3-(4-Chlorophenyl)propyl methyl ether

To a stirred solution of 3-(4-chlorophenyl)propanol (9.61 g, 54.17 mmol) and methyl iodide (7.0 ml, 112 mmol) in dry tetrahydrofuran (85 ml) under nitrogen was added 60% sodium hydride (2.83 g, 70.8 mmol) in portions. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was treated with ice/water (150 ml), extracted with methylene chloride (3×250 ml), and the combined organic extracts were washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo. Chromatography of the residual yellow oil on silica gel eluting with hexane afforded the title compound as a yellow oil (8.69 g, 86% from 3-(4-chlorophenyl)propionic acid) which was characterized by NMR spectral analysis.

1. extractionextracted with methylene chloride (3×250 ml)
2. washthe combined organic extracts were washed with water
3. dry with materialdried over anhydrous sodium sulfate
4. concentrationconcentrated in vacuo

ORD record

ord-8b45286a8ab04acca8d797bd1445f65a

Source dataset

uspto-grants-2003_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06506800B2