Potassium Carbonate → HCID 54426091, compound
Reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][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+]>COCCOC>[O:24]1[CH2:23][C@@H:22]1[CH2:21][O:1][C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[CH:4]=[O:5]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 2-hydroxy-5-methylbenzaldehyde (7.1 g), (R)-glycidyl 4-toluenesulphonate (11.9 g) and potassium carbonate (7.25 g) in anhydrous 1,2-dimethoxyethane (150 ml) was stirred and heated at 60° C. for 5 hours, allowed to stand at ambient temperature for 18 hours, heated at 60° C. for a further 8 hours then allowed to cool for 18 hours. The solvent was removed in vacuo and the residue partitioned between water (250 ml) and ether (250 ml). The mixture was filtered through Celite, the ether layer separated, washed with water and dried over magnesium sulphate. The solvent was evaporated and the residue purified by flash chromatography on silica eluting with a 1:1 mixture of ether and petroleum ether (b.p. 40-60° C.). Appropriate fractions were combined and the solvent evaporated to give (R)-2-(2,3-epoxypropoxy)-5-methylbenzaldehyde (8.91 g) as an oil.
Workup
- temperatureheated at 60° C. for a further 8 hours
- temperatureto cool for 18 hours
- customThe solvent was removed in vacuo
- customthe residue partitioned between water (250 ml) and ether (250 ml)
- filtrationThe mixture was filtered through Celite
- customthe ether layer separated
- washwashed with water
- dry with materialdried over magnesium sulphate
- customThe solvent was evaporated
- customthe residue purified by flash chromatography on silica eluting with a 1:1 mixture of ether and petroleum ether (b.p. 40-60° C.)
- customthe solvent evaporated
Sources & evidence
- ORD record
- ord-52b59e1794dd40929b6a51bb690edfe5
- Source dataset
- uspto-grants-1999_08
- Patent number
- US05935973
Reaction notes
Loading…