[C:1]1([OH:13])[CH:12]=[C:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH:5]=[C:3](O)[CH:2]=1.[Cl-].[NH4+:15].S(=O)(O)[O-].[Na+].[OH-].[NH4+].Cl>C(OCC)(=O)C>[OH:13][C:1]1[CH:2]=[C:3]([CH:5]=[C:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH:12]=1)[NH2:15]
Olivetol (1.8 g., 0.01 M), ammonium chloride (2.65 g., 0.05 M), sodium bisulfite (5.2 g., 0.05 M) and ammonium hydroxide (12.5 ml.) are combined and heated in a steel bomb at 230° C. for a half-hour. The bomb is then cooled, the contents dissolved in ethyl acetate (350 ml.). Hydrochloric acid (300 ml. of 10%) is added, the mixture stirred and then the organic layer separated. The extraction is repeated two more times. The aqueous acid solution is neutralized with 6 N sodium hydroxide and then extracted with chloroform (3×300 ml.). The combined chloroform extracts are dried and concentrated. The residue is taken up in ethyl acetate, decolorized with charcoal and concentrated. The addition of hexane to the residue causes it to crystallize: 270 mg.; m.p. 88°-91° C. When recrystallized from hot ethyl acetate-hexane (1-1) it melts at 95°-96° C.
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