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ChemicalBook CAS DataBase List 4-(CHLOROMETHYL)BENZYL ALCOHOL 99
16473-35-1

4-(CHLOROMETHYL)BENZYL ALCOHOL 99 synthesis

4synthesis methods
4-(Chloromethyl)benzoic acid

1642-81-5

4-(CHLOROMETHYL)BENZYL ALCOHOL  99

16473-35-1

Example 1: (1) Synthesis of [4-(chloromethyl)benzyl]alcohol: To a solution of tetrahydrofuran containing 4-(chloromethyl)benzoic acid (60 mL THF), 1M borane-THF solution (90 mL) was slowly added. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, methanol (50 mL) was added to quench the reaction. Subsequently, the solvent was removed by rotary evaporator and the obtained residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 4/1 to 3/1) to afford 4-(chloromethyl)benzyl alcohol (8.84 g, 96% yield) as a colorless solid.

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Yield: 96%

Reaction Conditions:

with borane-THF in tetrahydrofuran at 20;

Steps:

1.1 Example 1; (1) 4-CHLOROMETHYLBENZYL Alcohol
Example 1: (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, 96%) as a colorless solid.

References:

BAYER HEALTHCARE AG WO2003/106403, 2003, A1 Location in patent:Page 23

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