Acetone → (4-Chlorophenoxy)acetic acid

A mixture of 4-chlorophenol (500 mg), methyl bromoacetate (0.368 ml), cesium carbonate (1.9 g) and 5 ml of acetone was stirred at room temperature for 12 h. Ethyl acetate and water were then added to the reaction solution, and the organic phase was washed twice with water, dried over sodium sulfate and filtered, and the solvent was removed in vacuo. The crude product was dissolved in a 1:1 THF/water mixture (10 ml), and potassium hydroxide (417 mg) was added. The reaction was stirred at room temperature for 12 h. Ethyl acetate and water were then added to the reaction solution, and the aqueous phase was adjusted to pH 2 and extracted several times with ethyl acetate. The combined organic phases were washed twice with water, dried over sodium sulfate and filtered, and the solvent was removed in vacuo. The product with the molecular weight of 186.6 (C8H7ClO3) was obtained in this way; MS (ESI): 227.0 (M+CH3CN).

1. washthe organic phase was washed twice with water
2. dry with materialdried over sodium sulfate
3. filtrationfiltered
4. customthe solvent was removed in vacuo
5. dissolutionThe crude product was dissolved in a 1:1 THF/water mixture (10 ml), and potassium hydroxide (417 mg)
6. additionwas added
7. stirringThe reaction was stirred at room temperature for 12 h
8. additionEthyl acetate and water were then added to the reaction solution
9. extractionextracted several times with ethyl acetate
10. washThe combined organic phases were washed twice with water
11. dry with materialdried over sodium sulfate
12. filtrationfiltered
13. customthe solvent was removed in vacuo
14. customThe product with the molecular weight of 186.6 (C8H7ClO3) was obtained in this way

ORD record

ord-683ce7db48a5498ea3dd61deeb354a88

Source dataset

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07319108B2