Ethanol → (+/-)-6-Benzyloxy-2,5,7,8-tetramethylchroman2-acetic acid

Participants

Reaction Steps

To a solution of 6.09 g. of (±) -6-benzyloxy-2,5,7,8-tetramethylchroman-2-acetaldehyde in 280 ml. of ethanol was added a solution of 3.57 g. of silver nitrate in 42 ml. of H2O followed, dropwise over 0.5 hour, by a solution of 3.49 g. of sodium hydroxide in 100 ml. of H2O. The mixture was stirred at 23° for 2.0 hours, filtered, concentrated in vacuo, diluted with H2O, and extracted with ether. The aqueous solution was acidified with 1 N HCl and again extracted with ether. These latter extracts were washed with brine, dried over magnesium sulfate and stripped of solvents to give (±)-6-benzyloxy-2,5,7,8-tetramethylchroman2-acetic acid.

Provenance & Evidence