Hydrochloric Acid → Benzenepropanoic acid, 4-methoxy-beta-oxo-, ethyl ester
Reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1)=[O:3].[H-].[Na+].[C:14](=O)([O:18]CC)[O:15][CH2:16][CH3:17].Cl>CN(C)C=O>[CH2:16]([O:15][C:14](=[O:18])[CH2:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1)=[O:3])[CH3:17]Participants
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 4-methoxyacetophenone (100 g, 0.66 mol) in dry dimethylformamide (400 mL), 60% sodium hydride (34.3 g, 0.85 mol) was added slowly at 10° C. under a nitrogen atmosphere. This mixture was stirred at 25° C. for 30 minutes and again cooled to 10° C. This was added to solution of diethyl carbonate (94.5 g, 0.80 mol) and dissolved in minimum quantity of dry dimethylformamide at the same temperature. The mixture was then stirred at 25° C. for 5 to 6 hours and poured into ice cold water (100 mL) with vigorous stirring. The mixture was then acidified (pH˜6-7) using cold 2 N hydrochloric acid and extracted with ethyl acetate. The organic layers were collected, combined, washed with water, dried over anhydrous sodium sulphate, filtered and concentrated under vacuum to afford the desired compound as yellow oil (133 g). Yield: 90%.
Workup
- temperatureagain cooled to 10° C
- stirringThe mixture was then stirred at 25° C. for 5 to 6 hours
- extractionextracted with ethyl acetate
- customThe organic layers were collected
- washwashed with water
- dry with materialdried over anhydrous sodium sulphate
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-dcd3fdf5895349e7ac3c9f7a519ed5c6
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07820654B2
Reaction notes
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