Hydrochloric Acid → HCID 23500279, compound

Participants

Reaction Steps

A mixture of 9,12,15,25,28,31-hexa(p-toluenesulfonyl)-9,12,15,25,28,31-hexaaza-3,6-dioxatritriacontanol (1.30 g, 0.92 mmole), Na/Hg (10.85 g), and phosphoric acid disodium salt (1.96 g, 13.8 mmole) in methanol/dioxane (70 ml/40 ml) was heated to gentle reflux for 24 hours. Additional Na/Hg (2.0 g) was then added. The reaction mixture was maintained at reflux for another 24 hours, then cooled. The insoluble material was filtered and washed with CH3OH. The filtrate was concentrated to give an oily residue which was then treated with 2 N HCl (aq) and washed with CH2Cl2 (200 ml×2). The aqueous acidic solution was then made basic with 10% NaOH (aq), extracted with CH2Cl2 (250 ml×3), dried over MgSO4, filtered and concentrated to give a pale yellow oil (0.25 g, 55% crude yield) which was used further without purification. The reaction is shown schematically below:

Provenance & Evidence