5-Amino-2-hydroxytoluene → HCID 14500509, compound

Participants

Reaction Steps

A solution of 25 g (0.20 mol) of 4-amino-2-methylphenol in about 450 mL of acetone was stirred at room temperature and 20.6 g (0.09 mol) of 6-bromohexanoyl chloride was dripped in over 20 minutes. The reaction was stirred at room temperature for 3 hours then ice-cooled and filtered. The filtrate was stripped in vacuo to a residual oil which was triturated once in 225 mL of 1N HCl and then several times in cold water. The resulting gum was dissolved in absolute ethanol and 28 g of product (95%) were crystallized out by the addition of water, mp 111°-112° C. The product, which contained a small amount of 4-amino-2-methylphenol, was used as is in the following reaction.

Provenance & Evidence