Hive Novel Discourse

	Main Index Search Register Login Who's Online FAQ Links
	Main Index Search Register Login Who's Online FAQ Links

	2 Online, 0 Active		You are not logged in

This is a historical archiveThe forum is read-only. Private information has been removed. It is not possible to login.

	Novel Discourse

All posts Subject: Henry reaction with orthoformate water scavenger Please login to post

Rhodium
(Chief Bee)
06-04-03 22:43
No 437833
User Picture Henry reaction with orthoformate water scavenger
(Rated as: excellent)

Nitroalkene synthesis (Henry reaction) using trimethyl orthoformate to remove the water formed in the reaction: (MeO)₃CH + H₂O -> 2 MeOH + HCOOMe

1-(2,6-dimethoxyphenyl)-2-nitropropene

A mixture of nitroethane (3.4 g, 45 mmol), 2,6-dimethoxybenzaldehyde (7.0 g, 42 mmol), CH₃COOK (2.4 g, 35 mmol), methylamine hydrochloride (3.4 g, 35 mmol), trimethyl orthoformate (10 ml), and methanol (30 ml) was stirred at reflux for 7 h. The reaction mixture was poured into water and extracted with ethyl ether. After the usual work up, the crude product was recrystallized from MeOH-Et₂O to give 1-(2,6-dimethoxyphenyl)-2-nitropropene, 7.5 g (80%), mp 102-103°C.

Reference: Tetrahedron 46, 7483 (1990)

	https://the-hive.archive.erowid.org	the-hive@erowid.org



Powered by Non Sustainable Resources^TM v.5.2.2, (C) 2014, Honeydew Server Microsystems
Links Erowid Rhodium

	All posts		Subject: Henry reaction with orthoformate water scavenger		Please login to post


		Rhodium (Chief Bee) 06-04-03 22:43 No 437833				Henry reaction with orthoformate water scavenger (Rated as: excellent)
						Nitroalkene synthesis (Henry reaction) using trimethyl orthoformate to remove the water formed in the reaction: (MeO)₃CH + H₂O -> 2 MeOH + HCOOMe 1-(2,6-dimethoxyphenyl)-2-nitropropene A mixture of nitroethane (3.4 g, 45 mmol), 2,6-dimethoxybenzaldehyde (7.0 g, 42 mmol), CH₃COOK (2.4 g, 35 mmol), methylamine hydrochloride (3.4 g, 35 mmol), trimethyl orthoformate (10 ml), and methanol (30 ml) was stirred at reflux for 7 h. The reaction mixture was poured into water and extracted with ethyl ether. After the usual work up, the crude product was recrystallized from MeOH-Et₂O to give 1-(2,6-dimethoxyphenyl)-2-nitropropene, 7.5 g (80%), mp 102-103°C. Reference: Tetrahedron 46, 7483 (1990)

	All posts		End of thread