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ChemicalBook CAS DataBase List 3-Isopropoxy-benzoic acid Methyl ester

3-Isopropoxy-benzoic acid Methyl ester synthesis

2synthesis methods
-

Yield:350989-42-3 86%

Reaction Conditions:

with potassium carbonate in N,N-dimethyl-formamide at 65; for 3 h;Inert atmosphere;

Steps:

20.1 Step 1

Compound 20-1 (1.00 g, 6.57 mmol) was dissolved in N,N-dimethylformamide (10 mL), and isopropyl bromide (1.62 g, 13.1 mmol) and potassium carbonate (2.27 g, 16.4 mmol) were add. The reaction was stirred at 65° C. for 3 hours under nitrogen atmosphere. Water (30 mL) was added to the reaction mixture after the mixture was cooled to 25° C. and the mixture was extracted with ethyl acetate (50 mL×3). The combined organic layer was washed with saturated brine (40 mL×4), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subject to silica gel column chromatography (10:1 petroleumether/ethyl acetate, Rf=0.5) to give compound 20-2 (1.10 g, colorless oil); yield: 86%. (0319) 1H NMR: (400 MHz, CDCl3) δ 7.61 (d, J=7.6 Hz, 1H), 7.50 (s, 1H), 7.33 (t, J=7.6 Hz, 1H), 7.07 (d, J=7.6 Hz, 1H), 4.65-4.60 (m, 1H), 3.92 (s, 3H), 1.36 (d, J=6.0 Hz, 6H).

References:

US2021/300908,2021,A1 Location in patent:Paragraph 0316-0319

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