Hydrochloric Acid → HCID 13604200, compound

Participants

Reaction Steps

1.77 Grams of 1-amino-7-hydroxy-4,6-dimethylindane and 50 ml of ethanol solution containing 2.57 g of 3,5-di-tert-butyl-4-hydroxybenzaldehyde were stirred together at a room temperature for 2 hours. Then sodium borohydride solution was added gradually by small portions to the reaction mixture under an ice-cooling condition. The reaction mixture was further stirred at a room temperature for 2 hours, then was acidified by adding hydrochloric acid. Then the reaction mixture was concentrated to dryness by evaporating the solvent under a reduced pressure. To the residue obtained was added 100 ml of water, and further added an aqueous solution of sodium acetate to adjust the pH of the solution to about pH=8, then extracted with 100 ml of ethyl acetate. The extract was washed with water, dried with anhydrous magnesium sulfate, concentrated to dryness by evaporating the solvent under a reduced pressure. The residue obtained was dissolved in 50 ml of ethanol, and the pH of the solution was adjusted by adding ethanol saturated with hydrogen chloride gas to about pH=3, then the solution was concentrated to dryness by evaporating the solvent under a reduced pressure. The residue obtained was recrystallized from ether-n-hexane to obtain 0.77 g of 1-(3,5-di-tert-butyl-4-hydroxybenzyl)amino-4,6-dimethyl-7-hydroxyindane in the form of colorless needle-like crystals. Melting point: 154°-155° C.

Provenance & Evidence