Potassium Carbonate → HCID 22557679, compound
Reaction equation
O[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:10])[CH:9]=1)[CH:5]=[O:6].[C:11](=[O:14])([O-])[O-].[K+].[K+].[F:17][C:18]([F:22])([F:21])[CH2:19]I>CN(C=O)C>[F:17][C:18]([F:22])([F:21])[CH2:19][O:10][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([O:14][CH2:11][C:18]([F:22])([F:21])[F:17])[CH:9]=1)[CH:5]=[O:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 3,5-dihydroxybenzaldehyde (2.0 g, 14.5 mmol) in DMF (35 mL) was added potassium carbonate (11.0 g, 80.0 mmol) and 1,1,1-trifluoro-2-iodoethane (33.3 g, 160 mmol). The reaction mixture was heated I a sealed reactor at 50° C. for 7 days. The mixture was filtered and washed with ethyl acetate. The filtrate was added water and the organic phase isolated. The aqueous phase was extracted once more with ethyl acetated. The combined organic phases were dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography eluting with toluene to give 906 mg (18%) of 3,5-bis-(2,2,2-trifluoro-ethoxy)-benzaldehyde. 1H NMR (CDCl3, 300 MHz) δ: 4.43 (q, 4H), 6.85 (t, 1H), 7.15 (d, 2H), 9.95 (s, 1H).
Workup
- filtrationThe mixture was filtered
- washwashed with ethyl acetate
- additionThe filtrate was added water
- customthe organic phase isolated
- extractionThe aqueous phase was extracted once more with ethyl
- dry with materialThe combined organic phases were dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography
- washeluting with toluene
Sources & evidence
- ORD record
- ord-1f835fdf8d284f59af7fbb06bded0a82
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06555577B1
Reaction notes
Loading…