Potassium Carbonate → 3-Fluoro-4-propoxybenzoic acid
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].C([O-])([O-])=O.[K+].[K+].I[CH2:19][CH2:20][CH3:21]>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH2:19][CH2:20][CH3:21])[C:5]([OH:7])=[O:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 2 g of 3-fluoro-4-hydroxybenzoic acid and 5.31 g of K2CO3 in 50 ml of acetonitrile is refluxed for 24 hours, 0.5 ml of 1-iodopropane is added and the refluxing is continued for 7 hours. After cooling to AT, the reaction mixture is concentrated under vacuum, the residue is taken up with water, the mixture is extracted with EtOAc and the solvent is evaporated off under vacuum. The residue is taken up in 30 ml of EtOH, 5 ml of a concentrated NaOH solution are added, and the mixture is left to stir at 60° C. for 1 hour. The mixture is concentrated under vacuum, the residue is taken up with a 10% HCl solution, the mixture is extracted with DCM, the organic phase is dried over Na2SO4, and the solvent is evaporated off under vacuum. 0.8 g of the expected compound is obtained.
Workup
- temperatureis refluxed for 24 hours
- temperatureAfter cooling to AT
- concentrationthe reaction mixture is concentrated under vacuum
- extractionthe mixture is extracted with EtOAc
- customthe solvent is evaporated off under vacuum
- addition5 ml of a concentrated NaOH solution are added
- waitthe mixture is left
- concentrationThe mixture is concentrated under vacuum
- extractionthe mixture is extracted with DCM
- dry with materialthe organic phase is dried over Na2SO4
- customthe solvent is evaporated off under vacuum
Sources & evidence
- ORD record
- ord-49b94555a02744aaafff836236182d6d
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07915258B2
Reaction notes
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