Benzene → 3,4-dihydro-6-(1,1-dimethylethyl)-8-iodospiro[2H-1,3-benzoxazine-2,2'-tricyclo(3.3.1.13,7)decane]

Participants

Reaction Steps

A mixture of 2-aminomethyl-4-(1,1-dimethylethyl)-6-iodophenol (1.5 g., 0.005 mole), 2-oxotricyclo(3.3.1.1.3,7)-decane (0.75 g., 0.005 mole) and p-toluenesulfonic acid (50 mg.) in benzene (25 ml.) is refluxed under a Dean-Stark trap for 2 hr. The solution is cooled, filtered, and evaporated to dryness. The residue is crystallized from ethanol to obtain 3,4-dihydro-6-(1,1-dimethylethyl)-8-iodospiro[2H-1,3-benzoxazine-2,2'-tricyclo(3.3.1.13,7)decane] (1.4 g.), m.p. 165°-166° C.

Provenance & Evidence