Potassium Carbonate → 1-(2,3-Dichloro-4-butyrylphenoxy)cyclobutane-1-carboxylic acid

Temperature

65 °C

A mixture of 2,3-dichloro-4-butyrylphenol (7 g, 0.03 mole), ethyl 1-bromocyclobutanecarboxylate (10.23 g, 0.049 mole) and potassium carbonate (7.5 g, 0.054 mole) in N,N-dimethylformamide (60 ml) was stirred and heated at 65° C. for 18 hours. The reaction mixture was poured into ice water and the resulting mixture was extracted with ether. The ether extract was washed with a 1% sodium hydroxide solution, then with water and finally dried over MgSO4. The ether was evaporated in vacuo and the residue treated with acetic acid (60 ml) and 5% hydrochloric acid (15 ml). The mixture was stirred and refluxed overnight. The solvents were evaporated in vacuo. The residue was chromatographed over a column containing silica gel (140 g) using methylene chloride/tetrahydrofuran/acetic acid 50/1/1 as the eluent. The pertinent fractions were united, treated with toluene and evaporated in vacuo to obtain 1-(2,3-dichloro-4-butyrylphenoxy)cyclobutane-1-carboxylic acid as a liquid whose identity was confirmed by NMR and purity by thin layer chromatography.

1. extractionthe resulting mixture was extracted with ether
2. extractionThe ether extract
3. washwas washed with a 1% sodium hydroxide solution
4. dry with materialwith water and finally dried over MgSO4
5. customThe ether was evaporated in vacuo
6. additionthe residue treated with acetic acid (60 ml) and 5% hydrochloric acid (15 ml)
7. stirringThe mixture was stirred
8. temperaturerefluxed overnight
9. customThe solvents were evaporated in vacuo
10. customThe residue was chromatographed over a column
11. additioncontaining silica gel (140 g)
12. additiontreated with toluene
13. customevaporated in vacuo

ORD record

ord-73cd8f7c18c04b6f96cb517683a466ec

Source dataset

uspto-grants-1987_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04699926