3-BENZYLOXYCINNAMIC ACID

(.pound.)-3-(3-(Benzyloxy)phenyl)prop-2-enoic acid (4).(E)-3-(3-hydroxyphenyl)acrylic acid (100 g, 606 mmol) was charged to a 2 L jacketed reactor. The reactor was flushed with nitrogen, charged with 800 mL of anhydrous DMF, and agitation was started. Solid potassium carbonate (250 g, 1.81 mol) was charged to the reaction at a rate to maintain the batch temperature between 20° C.-30° C. Benzyl bromide (160 mL, 1.35 mol) was charged to the reaction, and the reaction was agitated at 35° C. for 4 hours and until conversion to the bis-benzyl adduct was >95percent. The reaction was cooled to 22° C. and 1200 mL of water was charged to the reaction. The reaction was cooled to 10° C., at which point, 800 mL of water was charged to the reaction over 100 minutes. The resulting mixture was agitated for 1 hour. The solids were collected by filtration and washed with water. The wet solids were charged back to the 2 L jacketed reactor followed by 650 mL of ethanol. The solution was warmed to 55° C., at which point, aqueous sodium hydroxide (2M, 790 mL) was charged to the reaction. The reaction was agitated at 55° C. for 45 minutes and until saponification was >98percent. The reaction was cooled to normal room temperature. 600 mL of aqueous HCl (3M) was charged to the reaction at 20° C. dropwise over 70 minutes to crystallize the desired product. The resulting mixture was agitated at normal room temperature for 1 to 18 hours. The solids were collected by filtration and washed with water followed by heptane. The solids were dried in a vacuum oven with a nitrogen stream at 50° C. for 18 hours to provide the desired product (E)-3-(3-(benzyloxy)phenyl)acrylic acid as a white solid (151.24 g, 100 wt percent, 98percent yield).

Molecular Weight:254.28
XLogP3:3.3
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:305
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes