I just found an article which for some reason tells about the preparation of a lot of interesting precursors:
J. Am. Chem. Soc. 78, 584-590 (1956)
(
https://www.thevespiary.org/rhodium/Rhodium/pdf/3-Phenyl-1-propylamine.diazotization.pdf)
Diazotization of 3-Phenyl-1-propylamineThe reaction of 3-Phenyl-1-propylamine with sodium nitrite and acid gave the following products:
30% Phenyl-3-Propanol (reflux with TsOH gives Allylbenzene)
19% Phenyl-2-Propanol (mild oxidation gives P2P in high yield)
12% Allylbenzene
9% Recovered starting amine
Note: This seems very related to Post 436273
(Aurelius: "On Diazotization and WizardX's site", Methods Discourse)Oxidation of AllylbenzeneAllylbenzene (0.30 g., 2.5 mmoles) was stirred with 5 ml. of 98-100% formic acid and 0.9 ml of 30% hydrogen peroxide. The reaction became homogeneous in about 15 minutes and was then allowed to stand at room temperature for several hours. The formic acid was removed under reduced pressure and the residue boiled under reflux with 20% aqueous sodium hydroxide containing a little ethanol. The saponification reaction mixture was diluted with water and the 3-phenylpropane-1,2-diol removed by continuous ether extraction.
Note: Interesting - It seems like allylbenzene undergoes performic oxidation...Oxidation of Phenyl-2-Propanol to P2P[P2Pol] (5.5 g., 0.041 mole) was stirred overnight at room temperature with 2.8 g. (0.028 mole) of chromium trioxide in 20 ml. of 80% acetic acid. Fractionation [Anal. Chem. 20, 361 (1948)] of the crude mixture of products under reduced pressure gave 0.3 g. of benzaldehyde (octahydroxanthene derivative, m.p. 205.5-206°C), 2.0 g. of [P2P], and 1.2 g. of a mixture of [P2Pol] (p-toluenesulfonate, m.p. 90.8-91°C) and [P2P] (2,4-dinitrophenylhydrazone, m.p. 152-153°C).
Note: The mp of Phenyl-2-Propanol tosylate mentioned. Post 102983
(Siegfried: "1-phenyl-2-tosyloxy-propane", Chemistry Discourse)Allylbenzene Hydrocinnamyl acetate, b.p. 133°C (18 mm.) (61 g., 0.34 mole) was passed over glass wool heated at 460-485°C. The pyrolysis product was washed with aqueous sodium carbonate solution, dried and distilled at atmospheric pressure. The yield of allylbenzene, b.p 150-160°C, was 31g (76%). On redistillation through a 36x1-cm. spinning-band column, most of the olefin was collected at 59-59.5°C.
Note: A novel synthesis of Allylbenzene?