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All posts Subject: Eugenol to Homogenol (3-EtO-4-OH-Allylbenzene) Please login to post

Rhodium
(Chief Bee)
07-17-03 23:28
No 448125
User Picture Eugenol to Homogenol (3-EtO-4-OH-Allylbenzene)
(Rated as: excellent)

Synthesis of 3-Ethoxy-4-Hydroxy-Allylbenzene from 3-Methoxy-4-Hydroxy-Allylbenzene (Eugenol)
Nenokischi Hirao
Bull. Chem. Soc. Japan 11, 179-184 (1936) (https://www.rhodium.ws/pdf/eugenol2homogenol.pdf)

I found this article in an abstract database, where they only told that it contained a procedure for converting the Methoxy group of Eugenol to the Ethoxy homolog (called Homogenol by the authors), with no further details given. Great, I thought, then it most definitely contains a procedure for demethylation of eugenol to form 3,4-Dihydroxyallylbenzene (5-allylpyrocatechol), an excellent precursor to safrole. However, when I actually found the article, I saw that it contained a rather byzantine route for the insertion of that extra CH₂ group.

However, the article contains some rather interesting chemistry anyway, and various compounds which very likely can be used as precursors to other substances than safrole.

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	All posts		Subject: Eugenol to Homogenol (3-EtO-4-OH-Allylbenzene)		Please login to post


		Rhodium (Chief Bee) 07-17-03 23:28 No 448125				Eugenol to Homogenol (3-EtO-4-OH-Allylbenzene) (Rated as: excellent)
						Synthesis of 3-Ethoxy-4-Hydroxy-Allylbenzene from 3-Methoxy-4-Hydroxy-Allylbenzene (Eugenol) Nenokischi Hirao Bull. Chem. Soc. Japan 11, 179-184 (1936) (https://www.rhodium.ws/pdf/eugenol2homogenol.pdf) I found this article in an abstract database, where they only told that it contained a procedure for converting the Methoxy group of Eugenol to the Ethoxy homolog (called Homogenol by the authors), with no further details given. Great, I thought, then it most definitely contains a procedure for demethylation of eugenol to form 3,4-Dihydroxyallylbenzene (5-allylpyrocatechol), an excellent precursor to safrole. However, when I actually found the article, I saw that it contained a rather byzantine route for the insertion of that extra CH₂ group. However, the article contains some rather interesting chemistry anyway, and various compounds which very likely can be used as precursors to other substances than safrole.

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