3-(4-Carboethoxy)phenyl propanal

Ethyl 4-iodobenzoate (200 g, 0.725 mol) and allyl alcohol (63 g, 1.087 mol) are added to a stirred suspension of Sodium bicarbonate (152 g, 1.812 mol), tetrabutyl-ammounium bromide (117 g, 0.362 mol) and Palladium (II) acetate (3.2 g, 0.014 mol) in DMF (600 mL). The reaction mixture is warmed to 75-80° C. for 3-3.5 hours and cooled to 40° C.-50° C. Toluene (1 L) is added to the reaction mixture with vigorous agitation and the mixture is stirred for 15 min at room temperature. The resulting mixture is filtered through a celite pad. The pad is washed with toluene (2.x.200 mL). The filtrate and wash are combined, washed with water (3.x.1 L), evaporated to constant weight at 30° C.-40° C. and 10 mmHg. The crude product 147.5 g (98.8percent, 84percent by HPLC) of 4-(3-Oxo-propyl)-benzoic acid ethyl ester as dark brown oil is obtained and can be used in the next step without further purification. 1H NMR (DMSO-d6): δ1.38(t, 3H), 2.81(t, 2H), 3.03(t, 2H), 4.39(q, 2H), 7.27(d, 2H), 7.98(d, 2H), 9.81 (s, 1H).A mixture of 150 g (0.54 mol) of ethyl 4-iodobenzoate, 47 g (0.81 mol) of allyl alcohol, 113.4 g (1.35 mol) of potassium hydrogen carbonate, 3.65 g (0.016 mol) of palladium acetate EPO This compound has been reported and fully characterised.1 To a stirred suspension oftetrabutylammonium bromide (552 mg, 1.71 mmol), sodium hydrogen carbonate (380 mg, 4.52 mmol) and 3Å molecular sieves (0.35 g) in DMF (6 mL) was added ethyl-4-iodobenzoate (296 μL, 1.76 mmol) and allyl alcohol (180 μL, 2.65 mmol) under a flow ofnitrogen. Palladium acetate (24.9 mg, 111 μmol) was added and and the reaction sealed andheated to 70oC. After stirring for 3 hours the mixture was filtered through celite, dilutingwith ethyl acetate (40 mL). This was washed with water (40 mL) and back extracted withethyl acatate (2 x 40 mL). The organic extracts were combined, dried (Na2SO4) andconcentrated. Purification by column chromatography (14-16percent EtOAc/Pet ether) gave 10 as a clear oil (135 mg, 0.65 mmol, 37percent).H (400 MHz, CDCl3): 9.82 (1H, s, CHO) 7.97(2H, d, J = 8.3 Hz, ArH), 7.26 (2H, d, J = 8.3 Hz, ArH), 4.36 (2H, q, J = 7.2 Hz, CH2CH3), 2.96 - 3.05 (2H, t, J = 7.5Hz, CH2), 2.76 - 2.86 (2H, t, J = 7.5Hz, CH2), 1.38 (3H, t, J = 7.2Hz, CH2CH3); C (100 MHz, CDCl3): 200.9, 166.6, 145.8, 130.0, 128.8, 128.4, 61.0, 44.9, 28.1, 14.4.A.

Molecular Weight:206.24
XLogP3:2.4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:6
Exact Mass:206.094294304
Monoisotopic Mass:206.094294304
Topological Polar Surface Area:43.4
Heavy Atom Count:15
Complexity:205
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes