Hydrazine hydrate (1:1) → 14-Aminotetradecan-1-ol
Reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]1C(=O)C2=CC=CC=C2C1=O.O.NN>CO>[NH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of N-(14-hydroxytetradecyl)phthalimide in 100 ml of methanol was added 0.87 g of hydrazine monohydrate and the mixture was heated under reflux for 3 hours. The reaction solution was distilled under reduced pressure and the residue was diluted with a 1N aqueous solution of sodium hydroxide and then extracted twice with chloroform. The organic layers were combined, washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and then distilled under reduced pressure. Chromatography over silica gel afforded the title compound as a colorless crystal.