Triethylamine → 4-Methylbenzoic acid butyl ester

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Microencapsulated Pd(OAc)2 (prepared as described in Example 1, 0.23 g, 2 mol %, based on palladium content) was added to a solution of 4-iodotoluene (1 mmol) and triethylamine (4 mmol) in 1,2-Dimethoxyethane/n-butanol (1:1, 10 mL). The reaction vessel was evacuated and purged with carbon monoxide (CO). The reaction mixture was stirred at 95° C. for 24 h under a CO atmosphere (using a balloon). The mixture was allowed to cool to room temperature, diluted with dichloromethane (50 mL) and filtered through a polyethylene frit (20-micron porosity). The filtrate was washed with water (2×20 mL) and dried (MgSO4). Evaporation under reduced pressure and purification by column chromatography gave butyl 4-methylbenzoate, 89%; IR: 1714; 1H NMR (400 MHz; CDCl3): 7.93 (2H, d, J 8.2), 7.23 (2H, d, J 8), 4.31 (2H, t, J 6.6), 2.41 (3H, s), 1.78-1.71 (2H, m), 1.49 (2H, sext, J 7.5) and 0.98 (3H, t, J 7.4); 13C NMR (CDCl3): 167.2, 143.8, 130.0, 129.4, 128.2, 65.0, 31.2, 22.0, 19.7 and 14.1.

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