Potassium Carbonate → HCID 53638351, compound
Reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[C:3]=1[CH:4]=[O:5].C1(C)C=CC(S(O[CH2:21][C@@H:22]2[O:24][CH2:23]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:21][C@@H:22]2[O:24][CH2:23]2)[C:3]=1[CH:4]=[O:5]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A stirred mixture of 2-chloro-6-hydroxybenzaldehyde (4.4 g), (R)-glycidyl 4-toluenesulphonate (5.0 g) and potassium carbonate (3.9 g) in dimethylformamide (120 ml) was heated at 60° C. for 5 hours then allowed to stand at ambient temperature for 18 hours. The solvent was removed in vacuo, water (60 ml) was added and the mixture extracted with ether (3×100 ml). The combined extracts were dried over magnesium sulphate and the solvent evaporated. The residue was purified by flash chromatography on silica eluting with a 1:1 mixture of petroleum ether (b.p. 60-80° C.) and dichloromethane followed by a 19:1 mixture of dichloromethane and industrial methylated spirit. Appropriate fractions were combined and the solvent was removed in vacuo to give (R)-2-chloro-6-(2,3-epoxypropoxy)benzaldehyde (2.8 g) m.p. 62-64° C.
Workup
- customThe solvent was removed in vacuo, water (60 ml)
- additionwas added
- extractionthe mixture extracted with ether (3×100 ml)
- dry with materialThe combined extracts were dried over magnesium sulphate
- customthe solvent evaporated
- customThe residue was purified by flash chromatography on silica eluting with a 1:1 mixture of petroleum ether (b.p. 60-80° C.) and dichloromethane
- additionfollowed by a 19:1 mixture of dichloromethane and industrial methylated spirit
- customthe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-5ca781ee6afa4f8fad0bfc003e5b6639
- Source dataset
- uspto-grants-1999_08
- Patent number
- US05935973
Reaction notes
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