Methyl 4-aminobenzoate synthesis
- Product Name:Methyl 4-aminobenzoate
- CAS Number:619-45-4
- Molecular formula:C8H9NO2
- Molecular Weight:151.16
150-13-0
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69-72-7
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619-45-4
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Yield:619-45-4 79%
Reaction Conditions:
Stage #1:4-amino-benzoic acid with potassium carbonate in N,N-dimethyl acetamide at 110; for 0.5 h;
Stage #2:methyl salicylate at 110; for 24 h;
Steps:
Methyl 2-Methoxybenzoate (3a); Typical Procedure
General procedure: A mixture of 2-methoxybenzoic acid (3.8 g, 25 mmol) and K2CO3 (2.07 g, 15 mmol) in DMA (50 mL) was stirred at 110 °C for 0.5 h. Methyl salicylate (5.70 g, 37.5 mmol) was added and the resulting mixture was stirred for 24 h. The solvent was then removed in vacuo. After cooling to r.t., K2CO3 (2.42 g, 17.5 mmol) and water (50mL) were added to hydrolyze the excess methyl salicylate. The resulting mixture was heated at 60 °C until methyl salicylate disappeared on TLC. Then, the solution was extracted with EtOAc (3 ×20 mL). The organic layer was washed with water, sat. aq NaCl solution,and dried (anhyd MgSO4). Evaporation of solvent in vacuoafforded methyl 2-methoxybenzoate (3.82 g, 92%). More than 90% of salicylic acid was recovered as a white precipitate by acidifying the aqueous phase with 1 M HCl.
References:
Chen, Si;Jia, Lei;Li, Xiaonan;Luo, Meiming [Synthesis,2014,vol. 46,# 2,art. no. SS-2013-H0569-OP,p. 263 - 268]
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1126-46-1
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