(4-BENZOYL-PHENOXY)-ACETICACID

General procedure: A solution of NaOH 1N (3.9 mmol) was added to esters 7-16(3.0 mmol) in EtOH (20 mL), and the mixture was stirred at r.t. for 10-15 h. The solvent was removed under reducedpressure and the residue was poured into water (20 mL) andacidified with conc HCl at 0 °C. The aqueous layer was extractedwith dichloromethane (3 20 mL) and then the organiclayer was dried over Na2SO4 and concentrated underreduced pressure. The residue was purified by crystallizationwith cyclohexane or chloroform affording desired acids 17-26 with good yields.General procedure: To a solution of 5a-i (1.0 eq.) in a mixture of equal amounts of THF and methanol (0.5 M solution) was added an aqueous 1 M solution of LiOH (5.0 eq.). After 1 hour at 100 °C th esaponification of the esters 6a-q was completed shown by TLC (EtOAc/Pet. ether 1/3). While the mixture was cooled on ice, the pH was adjusted to pH = 1 using a 2 M HCl solution (aq.). The resulting precipitate was collected by filtration, washed with water, Pet. ether and co-evaporated with acetone to dryness. 1.7.1. 2-(4-Benzoylphenoxy)acetic acid (6a).[21] White solids 1.37 g, yield = 95percent. 1H NMR (400 MHz, CDCl3 + drop of DMSO): δ 9.50 (s br, 1H), 7.82 (d, J = 8.4 Hz, 2H), 7.75 (d, J = 7.6 Hz, 2H), 7.58 (t, J = 7.6 Hz, 1H), 7.47 (t, J = 7.6 Hz, 2H), 7.00 (d, J = 8.8 Hz, 2H), 4.69 (s, 2H) ppm.General procedure: A solution of NaOH 1N (3.9 mmol) was added to esters 7-16(3.0 mmol) in EtOH (20 mL), and the mixture was stirred at r.t. for 10-15 h. The solvent was removed under reducedpressure and the residue was poured into water (20 mL) andacidified with conc HCl at 0 °C. The aqueous layer was extractedwith dichloromethane (3 20 mL) and then the organiclayer was dried over Na2SO4 and concentrated underreduced pressure. The residue was purified by crystallizationwith cyclohexane or chloroform affording desired acids 17-26 with good yields.General procedure: To a solution of 5a-i (1.0 eq.) in a mixture of equal amounts of THF and methanol (0.5 M solution) was added an aqueous 1 M solution of LiOH (5.0 eq.). After 1 hour at 100 °C th esaponification of the esters 6a-q was completed shown by TLC (EtOAc/Pet. ether 1/3). While the mixture was cooled on ice, the pH was adjusted to pH = 1 using a 2 M HCl solution (aq.). The resulting precipitate was collected by filtration, washed with water, Pet. ether and co-evaporated with acetone to dryness. 1.7.1. 2-(4-Benzoylphenoxy)acetic acid (6a).[21] White solids 1.37 g, yield = 95percent. 1H NMR (400 MHz, CDCl3 + drop of DMSO): δ 9.50 (s br, 1H), 7.82 (d, J = 8.4 Hz, 2H), 7.75 (d, J = 7.6 Hz, 2H), 7.58 (t, J = 7.6 Hz, 1H), 7.47 (t, J = 7.6 Hz, 2H), 7.00 (d, J = 8.8 Hz, 2H), 4.69 (s, 2H) ppm.

Molecular Weight:256.25
XLogP3:2.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:256.07355886
Monoisotopic Mass:256.07355886
Topological Polar Surface Area:63.6
Heavy Atom Count:19
Complexity:312
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes