Ethanol → 4-(4,4,4-Trifluorobutoxy)benzoic acid

To a stirred solution of ethyl 4-(4,4,4-trifluorobutoxy)benzoate (0.60 g, 2.17 mmol) in THF/water (3:1 v/v, 15 ml) at room temperature was added LiOH (0.11 g, 4.34 mmol) in one portion. The reaction mixture was stirred at room temperature for 18 h, then EtOH (15 ml) was added to give a clear solution and stirring was continued for 48 h. The solvents were removed under reduced pressure and to the residue was added water (30 ml). This was extracted with DCM (30 ml) and the aqueous phase was then acidified with 1 M HCl and extracted with EtOAc (3×30 ml). The combined organic extracts were washed with brine (30 ml) and dried (Na2SO4). The solvent was removed under reduced pressure to give the title compound (0.51 g, 95%) as a colourless solid which was used without further purification.

1. customto give a clear solution
2. stirringstirring
3. waitwas continued for 48 h
4. customThe solvents were removed under reduced pressure and to the residue
5. additionwas added water (30 ml)
6. extractionThis was extracted with DCM (30 ml)
7. extractionextracted with EtOAc (3×30 ml)
8. washThe combined organic extracts were washed with brine (30 ml)
9. dry with materialdried (Na2SO4)
10. customThe solvent was removed under reduced pressure

ORD record

ord-97603a2544bc432584fdfe94bf330875

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895313B2