Benzoic acid, 2,3-dichloro-, methyl ester

white crystals

A solution of 2, 3-dichlorobenzoic acid (1 00 g, 0.526 mol) in methanol (1 L), was addedH2S04 (20 ml). The solution was stirred under reflux overnight. The reaction mixture wascooled and concentrated. The resulting residue was diluted with water (1 00 ml) and ethylacetate (1 L). Then the organic layer was washed with aq. NaHC03 and brine, dried overNa2S04 , filtered and the filtrate was concentrated to provide the titled compound (99 g, 92percent), as a white solid; 1H NMR (300 MHz, CDCI3) 8 ppm 3.95 (s, 3 H), 7.27 (t, J=7.8 Hz, 1 H), 7.60 (dd, J=1.8 , 7.8 Hz, 1 H), 7.66 (dd, J=1.8 , 7.8 Hz, 1 H).a) A suspension of LiAIH4 (7.4 g, 0.195 mol) in THF (500 ml) was stirred at 0 C. A solutionof A suspension of 10.56 g of lithium aluminium hydride in 125 ml of THF is cooled to 0 C., a solution of 25.68 g of the compound obtained in the preceding step in 100 ml of THF is added dropwise, the temperature is allowed to return to RT and the mixture is kept stirred for 2 hours at RT. The reaction mixture is diluted by adding 250 ml of THF and hydrolysed by adding 11 ml of water, 11 ml of 4N NaOH and 33 ml of water. It is allowed to stand overnight at RT, the inorganic salts are filtered and the filtrate is concentrated under vacuum. 21.54 g of the expected product are obtained after drying under vacuum at 30 C.

Molecular Weight:205.03
XLogP3:3
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:203.9744848
Monoisotopic Mass:203.9744848
Topological Polar Surface Area:26.3
Heavy Atom Count:12
Complexity:172
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes