Isophthalic Acid → Benzoic Acid

Into a 50-mL round-bottom flask, was placed a solution of isophthalic acid (1.7 g, 10.24 mmol, 2.98 equiv) in dichloromethane (10 mL), EDC.HCl (660 mg, 3.44 mmol, 1.00 equiv), 4-dimethylaminopyridine (420 mg, 3.44 mmol, 1.00 equiv), and tert-butyl 3-(2-(2-(2-(methylamino)ethoxy)ethoxy)ethoxy)propanoate 8b (1 g, 3.44 mmol, 1.00 equiv). The resulting solution was stirred for 2 h at room temperature. The resulting mixture was washed with 2×20 mL of water and 1×20 mL of NH4Cl (aq). The mixture was dried over sodium sulfate and concentrated under vacuum. The crude product (1 g) was purified by reverse phase chromatography with a water/methanol gradient to yield 500 mg (33%) of 3-(14,14-dimethyl-12-oxo-3,6,9,13-tetraoxapentadecyl)carbamoyl)benzoic acid. as yellow oil. 1H-NMR (300 MHz, CD3OD, ppm): δ 8.087(s, 2H), 7.664-7.560(m, 2H), 3.785-3.499(m, 14H), 3.144-3.705(m, 3H), 2.489-2.448(m, 2H), 1.469-1.456(s, 9H). MS (ES, m/z): 440 [M+H]+.

1. customInto a 50-mL round-bottom flask, was placed
2. washThe resulting mixture was washed with 2×20 mL of water and 1×20 mL of NH4Cl (aq)
3. dry with materialThe mixture was dried over sodium sulfate
4. concentrationconcentrated under vacuum
5. customThe crude product (1 g) was purified by reverse phase chromatography with a water/methanol gradient

ORD record

ord-222a7f81b7414f1984e1e2b3fb1018e5

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09289430B2