Potassium Carbonate → Methyl 4-(2-chloroethyl)benzoate
Reaction equation
[Cl:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1.[C:13]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH3:13][O:9][C:8](=[O:10])[C:7]1[CH:11]=[CH:12][C:4]([CH2:3][CH2:2][Cl:1])=[CH:5][CH:6]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 4-(2-Chloro-ethyl)-benzoic acid (20 g, 108 mmol) in DMF (200 mL) is treated with K2CO3 (59.7 g, 432 mmol) and Mel (16.8 mL, 270 mmol) and stirred at 23 C for 18 h. The reaction mixture is diluted with EtOAc (450 mL) and washed with H2O (2×150 mL), saturated aqueous NaHCO3 (1×200 mL), brine (1×200 mL), dried (MgSO4), and concentrated to afford the title compound as a yellow oil.
Workup
- washwashed with H2O (2×150 mL), saturated aqueous NaHCO3 (1×200 mL), brine (1×200 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-b6e20fa4256f466195071bcec969ca70
- Source dataset
- uspto-grants-2000_07
- Patent number
- US06090825
Reaction notes
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