Sodium Carbonate → 3-Diallylaminophenoxyacetic acid methylester
Reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH2:12])[CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Br)C=C>[CH3:1][O:2][C:3](=[O:13])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N:12]([CH2:10][CH:9]=[CH2:8])[CH2:11][CH:6]=[CH2:7])[CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 45 °C
Procedure
22 g of 3-aminophenoxyacetic acid methylester are solved in 63 g allyl bromide. Subsequently, 10 g of sodium carbonate are added portionwise and the temperature is raised to 45° C. The reaction mixture is stirred at this temperature for 4.5 hours. The insoluble salt is filtered off and washed with 70 g of ethyl acetate. The combined filtrates are kept at 5° C. for 12 h. After the extraction with water, the organic phase is dried with sodium sulfate and the solvent is removed in vacuum (60° C., 28 mbar). Yield: 24 g (dark oil).
Workup
- filtrationThe insoluble salt is filtered off
- washwashed with 70 g of ethyl acetate
- waitThe combined filtrates are kept at 5° C. for 12 h
- extractionAfter the extraction with water
- dry with materialthe organic phase is dried with sodium sulfate
- customthe solvent is removed in vacuum (60° C., 28 mbar)
Sources & evidence
- ORD record
- ord-20083fe33d1a49cbb7c1acb3fb1d8cb1
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08088182B2
Reaction notes
Loading…