Triethylamine → m-Phenoxybenzyl cyanide

To a solution of 3-phenoxybenzylalcohol (25.0 g) and triethylamine (26.3 ml) in ethyl acetate (300 ml), methanesulfonyl chloride (14.6 ml) was added dropwise at 0° C. After stirring for 1 hour, the reaction mixture was washed with saturated aqueous sodium chloride, dried (MgSO4) and concentrated. The residue was dissolved in acetone (300 ml), admixed with sodium iodide (37.5 g) and then stirred for 1 hour. The reaction mixture was concentrated, and the residue was diluted with water and then extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and then concentrated. The residue was dissolved in dimethyl sulfoxide (100 ml) and stirred with sodium cyanide (7.35 g) for 15 hours at room temperature. The reaction mixture was diluted with ethyl acetate, washed with water, dried (MgSO4), and then concentrated. The residue was subjected to column chromatography on silica gel to obtain 3-phenoxyphenylacetonitrile (8.36 g, yield 32%) as an oil from a fraction eluted with ethyl acetate-hexane (1:7. v/v).

1. washthe reaction mixture was washed with saturated aqueous sodium chloride
2. dry with materialdried (MgSO4)
3. concentrationconcentrated
4. dissolutionThe residue was dissolved in acetone (300 ml)
5. stirringstirred for 1 hour
6. concentrationThe reaction mixture was concentrated
7. additionthe residue was diluted with water
8. extractionextracted with ethyl acetate
9. washThe ethyl acetate layer was washed with water
10. dry with materialdried (MgSO4)
11. concentrationconcentrated
12. dissolutionThe residue was dissolved in dimethyl sulfoxide (100 ml)
13. stirringstirred with sodium cyanide (7.35 g) for 15 hours at room temperature
14. additionThe reaction mixture was diluted with ethyl acetate
15. washwashed with water
16. dry with materialdried (MgSO4)
17. concentrationconcentrated

ORD record

ord-641bab9e2a0943d386ef1cd4bfeb9dbd

Source dataset

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06924300B2