Cesium carbonate → HCID 62703068, compound
Reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11].C(=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)S(O[CH2:24][C:25]([F:28])([F:27])[F:26])(=O)=O.[OH-].[Na+]>CN(C=O)C.O>[CH3:11][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[O:1][CH2:24][C:25]([F:28])([F:27])[F:26])[C:6]([OH:8])=[O:7]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of 4-hydroxy-3-methylbenzoic acid (10 g, 65.7 mmol) and cesium carbonate (64.2 g, 197 mmol) in DMF (150 mL) is added 2,2,2-trifluoroethyl trifluoromethanesulfonate (33.6 g, 145 mmol) at 0° C. The mixture is stirred at 0° C. for 10 minutes then at rt for 2 days. To the mixture, water (150 mL) and NaOH pellet (10 g) are added, and the mixture is stirred for 20 hours at rt. The mixture is diluted with water (100 mL). The aqueous phase is washed with ether (100 mL×2) and then acidified with conc. hydrochloric acid (pH 4) at 0° C. to give a white suspension. The precipitate is collected by filtration, washed with water and n-hexane, and dried in vacuo at 50° C. to give 14.8 g (96% yield) of the title compound as white solid.
Workup
- waitat rt for 2 days
- stirringthe mixture is stirred for 20 hours at rt
- washThe aqueous phase is washed with ether (100 mL×2)
- customacidified with conc. hydrochloric acid (pH 4) at 0° C.
- customto give a white suspension
- filtrationThe precipitate is collected by filtration
- washwashed with water and n-hexane
- customdried in vacuo at 50° C.
Sources & evidence
- ORD record
- ord-816dce2c7669495f8ae7df76c4fc868b
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09187475B2
Reaction notes
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