ChemicalBook CAS DataBase List Methyl 4-aminobenzoate

Methyl 4-aminobenzoate synthesis

12synthesis methods

Product Name:Methyl 4-aminobenzoate
CAS Number:619-45-4
Molecular formula:C8H9NO2
Molecular Weight:151.16

150-13-0 Synthesis

150-13-0
873 suppliers
$5.00/25g

119-36-8 Synthesis

119-36-8
967 suppliers
$5.00/10g

69-72-7 Synthesis

69-72-7
1192 suppliers
$5.00/10g

619-45-4
370 suppliers
$6.00/1g

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]