Ethyl 4-Hydroxyhydrocinnamate

General procedure: To a suspension of 3(4-hydroxyphenyl)propanoic acid 1 (0.05 mmol) in TMCS (0.1 mmol), the appropriate alcohol (1.0 mL) was added and the reaction mixture was stirred at 25°C. After 24 h, the reaction was stopped and evaporated under reduced pressure to afford 1a–d in quantitative yield without the need of purification: 3-(4-Hydroxyphenyl)propionic ethyl ester (1b) Oil; To a stirred solution of acid 9 (3 g, 18 mmol) in 30 mL of ethanol, under ice-cooling, was addedthionyl chloride (1.1 eq, 1.44 mL, 19 mmol) dropwise over 20 min. After stirring the reaction mixturefor 3 h at room temperature, methanol is distilled out and 25 mL of water is added. The separatedester is extracted with ethyl acetate and washed with 10 mL of saturated sodium bicarbonate solution.Evaporation of the ethyl acetate gave the ester in pure form. Yield 94percent, yellow liquid; 1H-NMR (CDCl3) δ : 1.22 (d, 3H, CH3), 2.59 (t, 2H, CH2), 2.87 (t, 2H, CH2), 4.12, q, 2H, CH2), 6.74 (d, 2H, 2.09, 6.48, H-3A-H-5A), 7.03 (d, 2H, 6.54, H-2A, H-6A). 13C-NMR (CDCl3) : 14.2 (CH3), 30.2 (CH2), 36.3 (CH2), 60.6 (CH2), 115.4 (C-3A, C-5A), 129.4 (C-2A, C-6A), 154.3 (C-4A), 173.6 (C=O). MS/EI: m/z (percent int. rel).194 (M+) 49percent, 142 (M - 74) 100percent.Alternative Synthesis Route for Compound 4'3-(4 Hydroxy-phenyl)-propionic acid ethyl ester (4'-1)4 drops of concentrated HCl are added, under stirring, to a solution of commercial 3-(4 Hydroxy-phenyl)-propionic acid (13.08 g; 78.79 mmol) in 100 mL of ethanol. The reaction medium is heated to reflux in a bath at 145° C. overnight. The ethanol is evaporated off and ethyl acetate is added. The organic phase is washed with a saturated NaHCOGeneral procedure: To asolution of α, β-unsaturatedester (1.0equiv) in EtOAc (0.2 M) was added Pd/C (5 wt.percent, 10 molpercent). The reaction mixturewas stirred at rt under H1)

Molecular Weight:194.23
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:194.094294304
Monoisotopic Mass:194.094294304
Topological Polar Surface Area:46.5
Heavy Atom Count:14
Complexity:171
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes