2,3-DICHLOROBENZYL ALCOHOL

white crystalline powder

General procedure: Aldehyde (1 mmol) was dissolved in 10 ml ofmethanol(ethanol for ketones) and cooled to 01. A suspension of LiAIH4 (7.4 g, 0.195 mol) in THF (500 ml) was stirred at 0 °C. A solutionof methyl 2, 3-dichlorobenzoate (49 g, 0.244 mol) in THF (50 ml) was added dropwiseinto the above mixture at 0 - 5 °C. Then the mixture was stirred at room temperature for 2h. The reaction mixture was quenched with ethyl acetate (15 ml), water (7.5 ml), 15percentNaOH (7.5 ml) and water (22.5 ml), filtered and the filtrate was concentrated. Theresulting residue was dissolved with DCM (500 ml) and washed with brine. The organiclayer was dried over Na2S04 , filtered and the filtrate was concentrated to provide the titledcompound (37 g, 88percent), as a white solid; 1H NMR (300 MHz, CDCI3) 8 ppm 4.81 (d, J=6.3Hz, 2 H), 7.24 (t, J=7.8 Hz, 1 H), 7.42- 7.45 (m, 2 H).b) A suspension of LiAIH4 (7.4 g, 0.195 mol) in THF (500 ml) was stirred at 0 C. A solutionof methyl 2, 3-dichlorobenzoate (49 g, 0.244 mol) in THF (50 ml) was added dropwiseinto the above mixture at 0 - 5 C. Then the mixture was stirred at room temperature for 2h. The reaction mixture was quenched with ethyl acetate (15 ml), water (7.5 ml), 15%NaOH (7.5 ml) and water (22.5 ml), filtered and the filtrate was concentrated. Theresulting residue was dissolved with DCM (500 ml) and washed with brine. The organiclayer was dried over Na2S04 , filtered and the filtrate was concentrated to provide the titledcompound (37 g, 88%), as a white solid; 1H NMR (300 MHz, CDCI3) 8 ppm 4.81 (d, J=6.3Hz, 2 H), 7.24 (t, J=7.8 Hz, 1 H), 7.42- 7.45 (m, 2 H).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.To a solution of To solution of MeOH (150 mL) containing 2, 3-dichlorobenzaldehyde (20 g, 0.11 mole), cooled in ice bath, was added a solution of NaBH4 (4.54 g, 0.12 mole) in 0.2 M NaOH (15 mL) slowly over 15 min under nitrogen atmosphere. After completion of the addition, the mixture was allowed to warm up gradually to rt, and stirred for 2.5 h at rt. The reaction was quenched by cooling the mixture and pouring it slowly to ice water (~700 mL). The mixing led to formation of white precipitates. After stirring for 30 min, the precipitates were collected on Bochner funnel; and the collected solid was dissolved in EtOAc (200 mL). The organic solution was washed with 0.1 M NaOH (150 mL), dried over Na2SO4, and concentrated to dryness in vacuo, yielding 2, 3-

Molecular Weight:177.02
XLogP3:2.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:175.9795702
Monoisotopic Mass:175.9795702
Topological Polar Surface Area:20.2
Heavy Atom Count:10
Complexity:108
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes