3-(carboxymethyl)benzoicacid

6M Sodium hydroxide (10 mL) was added to methyl 2- (3-cyanophenyl) acetate 74, (550 mg, 3.14 mmol) in methanol (10 mL) and then heated at 90° C. overnight. After concentrating the reaction mixture, the aqueous layer was washed with CH(iii) 3-Carboxymethyl-benzoic acid; 3-Cyanomethyl-benzonitrile (90 mg, 0.63 mmol) was suspended in conc. HC1 (3 ml), and heated to 80°C for 2 h. The solvent was then removed in vacuo to give the crude product, which was used without further purification. Yield: 110 mg, 97percent ; LC/MS tr 0.71 min; MS (ES+) m/z 181 (M+H)3-Carboxymethylbenzoic Acid 16. Methyl 3-(cyanomethyl)benzoate 15 (6.3 g, 36.0 mmol) was treated with H2SO4 (40percent, 108 mL) and refluxed for 3 h at 160°C. The reaction mixture was then slowly cooled, diluted with cold H3- (carboxymethyl) benzoicacid (0.500 g, 2.77 mmol) was dissolved in freshly distilled methanol (25 mL) . Added cone. H2S04 (8 drops) and refluxed in a Dean- Stark apparatus for 16 hrs. Reaction mixture was cooled to room temperature and concentrated in vacuo. The crude product was dissolved in CH2C12 (40 mL) and washed with sat. NaHC03 (30 mL x 2) and sat. NaCl (30 mL) . The organic layer was dried (anhydrous sodium sulfate) and concentrated in vacuo. The crude product was chromatographed on silica gel (Hexanes/EtOAc, 5:1) to yield target compound 76. Yield 547 mg, 95%. Rf = 0.60, H NMR (400 MHz, Chloroform-d) delta 7.98 (dd, J = 6.2, 1.6 Hz, 2H) , 7.51 (dt, J = 7.6, 1.6 Hz, 1H), 7.47 - 7.40 (m, 1H) , 3.94 (s, 3H) , 3.73 (s, 3H) , 3.71 (S, 2H) ; [M+H]+ = 209.25 (APCI+) .

Molecular Weight:180.16
XLogP3:1.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:180.04225873
Monoisotopic Mass:180.04225873
Topological Polar Surface Area:74.6
Heavy Atom Count:13
Complexity:212
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes