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At 250-350 °C in the presence of alumina, phenol (1) reacts with excess 1-propanol to give mainly (>90%) C'-alkylation to form mono-to penta-n-propylphenols plus some O-alkylation to form n-propyl aryl ethers. The principal component of the product mixture from 1 is 2,6-di-n-propylphenol (26-50 mol % yield). With 4-npropylphenol as substrate (instead of 1), tri-, tetra-, and penta-n-propylphenols are formed in 48-79% combined yield. On the average, only 3% of the total C3H7 groups in the product mixture are isopropyl ones. Deoxygenation is not observed. It is proposed that the principal products result from an S^-type reaction mechanism which involves nucleophilic attack (variously by C-2, C-4, C-6, or O) of an adsorbed ambident phenoxide ion onto C-l of an adsorbed n-propoxide group. n-Propylation at C-3 and C-5 of the phenol ring results from surface-catalyzed dienone-phenol rearrangement. Isopropylation may occur via a side reaction of SnI type.

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Phenylpropargylchlorid (Ia) liefert über das Phthalimid das Amin (Ic), das z.B. zum cis‐Cinnamyl‐amin (II) hydriert werden kann.