Water → HCID 14555675, compound

Participants

Reaction Steps

To a cold stirred suspension of 0.7 gms hydroxylamine hydrochloride and 1 gm sodium carbonate in 10 ml CH2Cl2 was added a solution of 2.1 gms 9(3-methoxyphenyl)nonanoyl chloride in 10 ml CH2Cl2. After stirring this mixture for 1/2 hr, 1.1 ml H2O was added, and the reaction was stirred overnight at room temperature. 30 ml water was added, the layers were separated, and the aqueous layer 3×50 ml extracted with CH2Cl2. The organic phases were combined, washed 2×20 ml water, 2×20 ml NaCl solution, dried over MgSO4, filtered, and evaporated in vacuo to give an oil which solidified on standing. The solid was crystallized from CH2Cl2 :hexanes but was still impure by thin layer chromatography. It was dissolved in 100 ml CHCl3, stirred with 20 gm silica gel, and filtered. The silica gel was suspended in 75 ml CHCl3, stirred, and filtered (process repeated three times). All filtrates were combined, evaporated in vacuo, and the residue recrystallized from CH2Cl2 :hexanes to give 0.7 gms product of m.p. 66°-8°. Elemental analysis: calculated C 68.79, H 9.02, N 5.01% found C 68.61, H 9.18, N 5.09%.

Provenance & Evidence