4-(CYANOMETHYL)BENZOIC ACID

Methyl 4-(cyanomethyl)benzoate (25g, 0.14mol) dissolved in 300mL methanol was add 160mL 1N NaOH and refluxed for3 hours. Most of the solvent was removed in vacuo. The residue was added 500mL water and acidified to pH 2–3 with concentrated HCl. The generated solid was filtered, washed with water and dried to give the title compound as white solid (21.2g, 92.2percent): E) 160 mL of 1N sodium hydroxide solution was added 300 mL of methanol solution of methyl cyanomethylbenzoate (25 g, 0.14 mol)And the mixture was refluxed for 3 hours. Steam to most of the solvent by adding 500mL of water, concentrated hydrochloric acid acidification to pH = 2-3, precipitated a large number of white solidbody. Filtered, washed with water and dried to give 21.2 g of 4I in 92.2percent yield.To a stirred solution of methyl 4-(cyanomethyl)benzoate (10 g, 60 mmol) in THF (500 ml) a solution of LiOH (2.90 g, 70 mmol) in water (600 ml) was added. It was stirred at room temperature for 16h. The mixture was concentrated in vacuo and onto the aqueous phase left a solution of HCI 35percent (6ml) was added. The solid obtained was filtered, washed with water and hexane and dried in vacuo at 40°C for 64h. It was treated with hexane (100 ml) stirring for 1 h. The solid obtained was filtered and dried to yield 7.95 g (86percent) of the title compound.LRMS: m/z 260 (M-1VRetention time: 2.10 min (method A)PREPARATION 131.1.d. A solution of 4-bromomethyl-benzoic acid (4.0 g, 18.6 mmol) in acetonitrile (186 mL) was treated with a solution of sodium cyanide (1.0 g, 20.4 mmol) and sodium hydroxide (0.74 g, 18.6 mmol) in water (24 mL). A solution of 4-bromomethyl-benzoic acid (4.0 g, 18.6 mmol) in acetonitrile (186 mL) was treated with a solution of sodium cyanide (1.0 g, 20.4 mmol) and sodium hydroxide (0.74 g, 18.6 mmol) in water (24 mL).

Molecular Weight:161.16
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:161.047678466
Monoisotopic Mass:161.047678466
Topological Polar Surface Area:61.1
Heavy Atom Count:12
Complexity:208
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes