Sodium Hydroxide → 2-Chloro-6-hydroxybenzonitrile

To a solution of 18-crown-6 (3.96 g, 15 mmol) in 30 mL of acetonitrile were added dry potassium acetate (1.47 g, 15 mmol) and 2-chloro-6-fluorobenzonitrile (1.56 g, 10 mmol). The reaction was refluxed under nitrogen for 25 hours, then cooled to room temperature. Sodium hydroxide (2 mL of a 10M solution, 20 mmol) and water (5 mL) were added, and the reaction stirred at room temperature for two hours. The acetonitrile was removed on a rotary evaporator, and the residue was taken up in ether and water. The basic aqueous layer was washed three times with ether. The aqueous layer was then made acidic with HCl, and the product extracted into ether. The ether layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting solid was crystallized from water/methanol to yield 1.11 g of 3-chloro-2-cyanophenol.

1. temperatureThe reaction was refluxed under nitrogen for 25 hours
2. customThe acetonitrile was removed on a rotary evaporator
3. washThe basic aqueous layer was washed three times with ether
4. extractionmade acidic with HCl, and the product extracted into ether
5. dry with materialThe ether layer was dried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customThe resulting solid was crystallized from water/methanol

ORD record

ord-e4ae1429ada4465dbfcfb4127a0253af

Source dataset

uspto-grants-2000_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06022894