Methanol → Methyl 4-(chloromethyl)benzoate
Reaction equation
[Cl:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.S(=O)(=O)(O)O.[CH3:17]O>>[CH3:17][O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:3]([CH2:2][Cl:1])=[CH:4][CH:5]=1Participants
4
Procedure
4-Chloromethylbenzoic acid (2.0 g) was dissolved in 300 ml of methanol and 0.5 ml concentrated sulphuric acid was added. The mixture was stirred at room temperature for eight days. Methanol was evaporated and the residue was dissolved in ethyl acetate. The organic layer was washed with saturated NaHCO3-solution, dried with Na2SO4 and evaporated to yield 4-chloromethylbenzoic acid methyl ester.
Workup
- customMethanol was evaporated
- dissolutionthe residue was dissolved in ethyl acetate
- washThe organic layer was washed with saturated NaHCO3-solution
- dry with materialdried with Na2SO4
- customevaporated
Sources & evidence
- ORD record
- ord-92a9fcefdd594bdfa9d078c1d4ed2b55
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07482340B2
Reaction notes
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