Iodoethanol → Valproic Acid

Temperature

100 °C

To the product of Example 87 (4.87 g, 30 mmol), 2-iodoethanol (5.16 g, 30 mmol) was added with stirring and cooling in an ice bath. The neat mixture was then heated to 100° C. in a water bath for 10 minutes, then removed from the heat and stirred for an additional 10 minutes. The reaction mixture was then dissolved in 50 ml of ether, washed with water (1×30 ml), 5% NaOH (2×30 ml), and again with water (2×30 ml). The ether layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. A light yellow liquid product was obtained in 67% yield from valproic acid (6.0 g). Silver nitrate gave a bright yellow precipitate. NMR analysis confirmed the identity of the product.

1. temperaturecooling in an ice bath
2. customremoved from the
3. temperatureheat
4. stirringstirred for an additional 10 minutes
5. dissolutionThe reaction mixture was then dissolved in 50 ml of ether
6. washwashed with water (1×30 ml), 5% NaOH (2×30 ml)
7. dry with materialThe ether layer was dried over anhydrous sodium sulfate
8. customthe solvent was removed under reduced pressure

ORD record

ord-b34f90a0f2c94285b4d300023a88b43e

Source dataset

uspto-grants-1996_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05525727