Dimethylformamide → Ethyl 4-ethoxy-3-methylbenzoate
Reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[CH3:11].[C:12](=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH3:20].CN(C)[CH:23]=[O:24]>O.CCOCC>[CH2:19]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:24][CH2:23][CH3:12])=[O:8])=[CH:4][C:3]=1[CH3:11])[CH3:20]Participants
7
Conditions
- Temperature
- 45 °C
Procedure
To a solution of 4-hydroxy-3-methyl-benzoic acid (1.00 g, 6.57 mmol) in N,N-dimethylformamide (10 mL) was added potassium carbonate (2.73 g, 19.7 mmol) and bromoethane (3.58 g, 2.44 mL, 32.9 mmol). The reaction mixture heated at 45° C. for 48 h in a sealed tube. The reaction mixture allowed to cool then diluted with water and ether. The ether layer was washed with 50% saturated NaHCO3 (50 mL) and brine (50 mL), dried over Na2SO4, and concentrated in vacuo to provide ethyl 4-ethoxy-3-methylbenzoate as an orange-colored oil. The crude product was taken directly to the next step. ESI-MS m/z calc. 208.10994. found 209.3 (M+1)+; Retention time: 1.78 minutes (3 min run).
Workup
- temperatureto cool
- washThe ether layer was washed with 50% saturated NaHCO3 (50 mL) and brine (50 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-d6136211d915438d898700259a70ef57
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181273B2
Reaction notes
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