3-[4-(BENZYLOXY)PHENYL]ACRYLICACID

General procedure: To a stirred solution of compounds 25–29 (2.00g), triethyl phosphonoacetate (1.1 equiv.), and potassium carbonate (2.0 equiv.) in dichloromethane/N, N-dimethylformamide (2:1, 15mL) was added a catalytic amount of DBU (0.03 equiv.). The reaction mixture was stirred at room temperature (compounds 25, 27, and 29) or 70°C (26, and 28) for 24–36h. After removal of dichloromethane by evaporation, ice water was added to the reaction mixture which was then stirred for 30min to give precipitates. After filtration, the filter cake was washed with plenty of water, and dried to produce ethyl cinnamates 30–34 as a white or grey solid in yields of 95–98percent. The ethyl cinnamates were used directly in the next reaction without characterization. Ethyl cinnamates 30–34 (2.57–4.11g) were added to a 100mL round-bottom flask and 1, 4-dioxane (20mL) and 1N−NaOH aqueous solution (8.0–16.0 equiv.) were added subsequently. The reaction mixture was stirred at room temperature for 48h. After completion of the reaction, the reaction mixture was acidified until pH 2 using 2N−HCl aqueous solution. The reaction mixture was stirred at room temperature for 30min and then the resulting solid was filtered. The filter cake was washed with a plenty of water, and dried to give the cinnamic acid derivatives 35–39 as a white or grey solid in yields of 100percent.General procedure: Compounds 21–25 (2.57–4.11 g) were added to a 100 mL roundbottomflask and 1, 4-dioxane (20 mL) and 1 N-NaOH aqueous solution(8.0–16.0 equiv.) were added subsequently. The reaction mixture wasstirred at room temperature for 48 h. After completion of the reaction, the reaction mixture was acidified until pH 2 by 2 N-HCl aqueous solution.The reaction mixture was stirred at room temperature for 30 minand then the resultant solid was filtered. The filter cake was washedwith a plenty of water, and dried to give the cinnamic acid derivatives26–30 as a white or grey solid in yields of 100percent.General procedure: A mixture of 3, 4-dihydroxy cinnamic acid or p-hydroxy cinnamic acid (1.0 mmol) , K2CO3 (1.5 mmol), benzyl bromide (4.0 mmol) and acetone (30 mL) were heated under reflux for 12 h, then cooled to room temperature. To the cooled slurry was added KOH (1.2 mmol) and stirring was continued for 10 h to saponify the ester. The solvent was removed, the residue taken up in H2O (50 mL), washed with Et2O (40 mL) and acidified with 3 M HCl. The solution was extracted with Et2O (3×20 mL), dried over MgSO4, and concentrated in vacuo to afford substituted cinnamic acids after recrystallization (MeOH).To weighed coumaric acid (7 g, 42.6 mmol) was added absolute ethanol (40 mL) to get a clear solution. Followed by addition of benzyl bromide (15 g, 10.6 mL, 87.7 mmol) and aqeous solution of base, NaOH (8.5 g, 212 mmol, in 40 mL of distilled water) stirred for 5 minutes to get clear solution and then reaction mixture was refluxed continuously for 36 hrs. On complete conversion of coumaric acid (TLC) reaction mixture was allowed to cool in an ice bath and this ethanolic reaction mixture was poured in an beaker (1 Litre) containing crushed ice subsequently queched carefully using HCl (5N) to get solid compound precipitate which was filtered washed with plenty of water, dried to get off white solid compound, (E)-3-(4-(benzyloxy)phenyl)acrylic acid 18 (10.3 g, 95percent ).

Molecular Weight:254.28
XLogP3:3.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:254.094294304
Monoisotopic Mass:254.094294304
Topological Polar Surface Area:46.5
Heavy Atom Count:19
Complexity:297
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes