Ethylene carbonate → 4-(2-Hydroxyethoxy)-3-methylbenzaldehyde
Reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:10].C([O-])([O-])=O.[K+].[K+].C1(=O)O[CH2:20][CH2:19][O:18]1>CN(C=O)C>[OH:18][CH2:19][CH2:20][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:10]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
To a solution of 4-hydroxy-3-methylbenzaldehyde (1.10 g, 8.08 mmol) in anhydrous DMF (12 mL) was added K2CO3 (2.23 g, 16.16 mmol) and ethylene carbonate (1.42 g, 16.16 mmol) at room temperature. The resulting reddish-orange suspension was stirred at 110° C. for 6 hours under nitrogen. DMF was removed and the residue was diluted with water (50 mL) and dichloromethane (50 mL). The organic phase was separated, and the aqueous phase was extracted with dichloromethane (2×20 mL). The combined organic phase was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain 4-(2-hydroxy-ethoxy)-3-methylbenzaldehyde as a brown oil. Yield: 1.46 g (100%).
Workup
- customDMF was removed
- additionthe residue was diluted with water (50 mL) and dichloromethane (50 mL)
- customThe organic phase was separated
- extractionthe aqueous phase was extracted with dichloromethane (2×20 mL)
- washThe combined organic phase was washed with brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-1d28e6dbfbdc4ff1bce5d87a8e0b5628
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238640B2
Reaction notes
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