Oxalyl chloride → 2-(3-Hydroxypropyl)benzonitrile

Temperature

20 °C

A solution of 3-(2-cyanophenyl)propanoic acid (Example 323b, 4.36 g) in DCM (40 mL) was treated with oxalyl chloride (3.26 mL) under nitrogen. The resulting solution was stirred at 20° C. for 1 h. The reaction mixture was evaporated to dryness, azeotroped with toluene. The solid was dissolved in THF (30 mL) and sodium borohydride (1.883 g) was added. The mixture was stirred at 20° C. for 16 h. Further Sodium borohydride (1.883 g) added and stirred for 4 h. The reaction required a further 3 days and a further sodium borohydride (18.83 g). The reaction mixture was evaporated, diluted with water (200 mL), and extracted with ethyl acetate (200 mL). The organic was dried (MgSO4), filtered and evaporated to give the subtitle compound as an oil (3.83 g). 1H NMR δ (DMSO-d6) 7.78 (d, 1H), 7.68-7.62 (m, 1H), 7.50 (d, 1H), 7.44-7.38 (m, 1H), 3.02 (t, 2H), 2.62 (t, 2H)

1. customThe reaction mixture was evaporated to dryness
2. customazeotroped with toluene
3. dissolutionThe solid was dissolved in THF (30 mL)
4. additionsodium borohydride (1.883 g) was added
5. stirringThe mixture was stirred at 20° C. for 16 h
6. additionFurther Sodium borohydride (1.883 g) added
7. stirringstirred for 4 h
8. customThe reaction
9. waitrequired a further 3 days
10. customThe reaction mixture was evaporated
11. additiondiluted with water (200 mL)
12. extractionextracted with ethyl acetate (200 mL)
13. dry with materialThe organic was dried (MgSO4)
14. filtrationfiltered
15. customevaporated

ORD record

ord-ef0dcb35e0ca4b70b4151c875b28b38d

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299246B2