4-Hydroxybenzyl Alcohol → HCID 11469652, compound

Participants

Reaction Conditions

Reaction Steps

300 ml of dichloromethane followed by 60 g of triethylamine are added to 30 g of 4-hydroxymethyl-phenol introduced into a 500 ml flask maintained under a hydrogen atmosphere. The temperature of the obtained solution is brought to 10° C. and 64 g of trimethylsilyl chloride are added thereto in about one hour, keeping the temperature at 10° C. Thus, the temperature is left to spontaneously rise to 25° C., maintaining such conditions for one hour. Then, the reaction of the substrate is controlled under TLC. Upon ascertaining the disappearance of the initial product, 200 ml of an aqueous saturated NaCl solution are added and the two-phase system is stirred vigorously for 10′ and then the two phases are decanted. The lower organic phase is washed with two 200 ml portions of deionised water and then concentrated to residue, obtaining a yellowish oil. Such residue is recovered using 500 ml of DMF in a 2-liter flask and a solution constituted by 3 g of Lithium acetate in 60 ml of water is added to the obtained solution. The mixture is maintained at 25° C. for one hour, then the removal of the trimethylsilyl group on the phenolic hydroxyl is controlled under TLC. Then, 650 ml of a saturated NaCl solution and 455 ml of toluene are added to the reaction mixture and the mixture is stirred vigorously for 10′, then the two phases are left to decant. The upper organic phase is then washed with two 650 ml portions of deionised water and concentrated under vacuum, obtaining 33 g of the desired product (70% yield).

Provenance & Evidence