methyl 2-butoxy-4-methoxybenzoate synthesis

Yield:942132-98-1 78%

Reaction Conditions:

Stage #1: 4-methoxymethylsalicylatewith potassium carbonate in N,N-dimethyl-formamide at 20; for 1 h;
Stage #2: 1-iodo-butane in N,N-dimethyl-formamide; for 20 h;

Steps:

22.1 Step 1:

A mixture of 2-hydroxy-4-methoxy-benzoic acid methyl ester (A) (0.461 g, 2.53 mmol) in DMF anhydrous (17 mL) and K₂CO₃ (0.7 g, 5.07 mmol) under N₂ atmosphere was stirring at room temperature for 1 hour. Afterwards, 1-iodobutane (0.43 mL, 3.80 mmol) is added and the mixture is stirred for 20 hours.After evaporation of the solvent to reduced pressure, ethyl acetate (100 mL) was added and the solution was washed with water (100 mL). The combined organic extracts were washed with saturated NaCl solution and dried with Na₂SO₄. Evaporation of the solvent under reduced pressure gave 0.47 g (78%) of 2-Butoxy-4-methoxy-benzoic acid methyl ester (F) as a white solid.Purification: was not required.Yield: 0.47 g (78%) as a white solid.¹H-NMR (CDCl₃, 400 MHz, ppm): 7.84 (dd, J=8.34, 0.58 Hz, 1H), 6.50-6.45 (m, 2H, H2), 4.01 (t, J=6.49, 6.49 Hz, 2H), 3.85 (s, 3H), 3.84 (s, 3H), 1.87-1.77 (m, 2H), 1.54 (qd, J=14.75, 7.37 Hz, 2H), 0.98 (t, J=7.40 Hz, 3H)¹³C-NMR (CDCl₃, 100 MHz, ppm): 166.33, 164.07, 160.84, 133.76, 112.62, 104.54, 99.86, 68.59, 55.42, 51.56, 31.15, 19.18, 13.81ESI-MS[M+H]⁺ 239

References:

US2009/69430,2009,A1 Location in patent:Page/Page column 24