4-(CHLOROMETHYL)BENZYL ALCOHOL99

(1) [4-CHLOROMETHYLBENZYL] Alcohol To a solution of 4-chloro-4-toluic acid in tetrahydrofuran (THF, 60 [ML)] was added 1 M borane THF solution (90 [ML).] The mixture was stirred at room temperature overnight and quenched by addition of methanol (50 ml). The solvent was evaporated off and the residue was purified by silica gel column chromatography (hexane/ethyl acetate = 4/1 to 3/1) to obtain 4-chloromethylbenzyl Alcohol (8.84 g, 96percent) as a colorless solid.Into a 2000-mL round-bottom flask was placed a solution of 4-(chloromethyl)benzoic acid 9a (50 g, 293 mmol) in THF (200 mL). This was followed by the addition of 1 M BH10611] Into a 2000-mE round-bottom flask was placed asolution of 4-(chloromethyl)benzoic acid 9a (50 g, 293mmol) in THF (200 mE). This was followed by the addition of1 M 13H3/THF (586 mE, 586 mmol) dropwise with stirring at00 C. over 1 hr. The resulting solution was stirred for 4 hat rt.The reaction was then quenched by the addition of 600 mE of1 N Rd. The solution was extracted with 500 ml of ethylacetate. The organic layer was washed with 300 ml of sodium carbonate (aq.), and 300 ml of brine. The organic layer was dried over sodium sulfate and concentrated under vacuum giving 9b (35 g, 76percent) as a white solid. ‘H NMR (400 MHz, CDC13) 4.50 (d, J=4.8 Hz, 2H), 4.75 (s, 2H), 5.21 (t, J=4.8 Hz, 1H), 7.32 (d, J=7.6 Hz, 2H), 7.39 (d, J=7.6 Hz, 2H).A round bottom flask was charged with 138 g (1 mol) of 1, 4-benzene dimethanol, 690 g of toluene was added and stirred. 203 g of an aqueous HCl solution (concentration: 35percent to 37percent) was gradually added dropwise to the round bottom flask, and the temperature was raised to 50°C and further stirred for 2 hours. When the reaction was completed, the aqueous layer was removed and washed with 5percent NaHCO3 aqueous solution and water. Water was removed using MgSO4, filtered and concentrated to give 141 g of a compound of formula (i).53.2 g of sodium borohydride, 530 g of tetrahydrofuran and 266 g of N, N-dimethylformamide were added to a three-necked flask equipped with a stirrer, a reflux condenser and a dropping funnel, and a solution of 266 g of chloromethylbenzoyl chloride in 130 g of tetrahydrofuran And the mixture was stirred at room temperature for 1 hour. 530 g of water of manufacture, 293 g of 10percent hydrochloric acid aqueous solution and 1060 g of ethyl acetate were added to the reaction solution, and the mixture was separated, washed with 665 g of sodium carbonate aqueous solution, and then dried with anhydrous sodium sulfate. The crude product obtained by distilling off the solvent was purified with 100 g of toluene to obtain 147.7 g (yield 66.9percent) of the title compound as white crystals.

Molecular Weight:156.61
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:156.0341926
Monoisotopic Mass:156.0341926
Topological Polar Surface Area:20.2
Heavy Atom Count:10
Complexity:87.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes