Hydrazine → HCID 136093926, compound

HRID 477578Notes

Reaction equation

HRID 477578 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16](=O)[CH2:17][CH2:18][C:19]([O:21]C)=O)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[NH2:24][NH2:25].CCCCCC.C(OCC)(=O)C>C(O)C>[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[CH2:17][CH2:18][C:19](=[O:21])[NH:24][N:25]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 9321HydrazineHCID 14847528HCID 14847528, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 136093926HCID 136093926, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 22 g (0.07 mol) methyl 4-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-oxo-butanoate and 6.8 g (0.18 mol) of 85% aqueous hydrazine in 250 ml of ethanol is heated under reflux. The reaction is considered complete by the disappearance of the starting material as indicated by TLC analysis (silica gel; 7/3: hexane/ethyl acetate). Upon cooling the reaction mixture, 18.0 g (85% yield) of white crystals are collected by filtration: mp 200°-203° C.; IR (CH2Cl2) 3640, 3420, 3250 and 1680 cm-1.

Workup

  1. temperatureis heated
  2. temperatureunder reflux

Sources & evidence

ORD record
ord-01dda2b188f843499cc7bba2db992c46
Source dataset
uspto-grants-1989_12
Patent number
US04888423

Reaction notes

Loading…