Methanol → Methyl 4-(aminomethyl)benzoate
Reaction equation
[NH2:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.O=S(Cl)Cl.[CH3:16]O>>[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([O:9][CH3:16])=[O:8])=[CH:10][CH:11]=1Participants
4
Conditions
- Temperature
- 70 °C
Procedure
4-aminomethyl benzoic acid (6.69 g, 44.09 mmol) was dissolved methanol (200 mL). SOCl2 (12 mL) was added via syringe. The mixture was stirred at 70° C. for 3.5 h. After cooling, the reaction mixture was evaporated and the crude product was dissolved in CH2Cl2 (500 mL). The organic layer was washed with aqueous K2CO3 10% (300 mL), dried with MgSO4, filtered and evaporated. Methyl 4-(aminomethyl)benzoate was obtained (5.78 g, 79%) as a white solid.
Workup
- temperatureAfter cooling
- customthe reaction mixture was evaporated
- dissolutionthe crude product was dissolved in CH2Cl2 (500 mL)
- washThe organic layer was washed with aqueous K2CO3 10% (300 mL)
- dry with materialdried with MgSO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-0ca716a1e39a41e5b1976c8c68df1015
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07923579B2
Reaction notes
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