Isopropanol → HCID 22408759, compound

HRID 1609140Notes

Reaction equation

HRID 1609140 reaction equation
[C:1]([O:5][O:6][C:7]([O:16][O:17][C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:15])[CH2:8][CH2:9][C:10](OCC)=[O:11])([CH3:4])([CH3:3])[CH3:2].[NH2:22][NH2:23].C(O)(C)C>O>[C:1]([O:5][O:6][C:7]([O:16][O:17][C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:15])[CH2:8][CH2:9][C:10]([NH:22][NH2:23])=[O:11])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 9321Hydrazine2×HCID 21406601HCID 21406601, compound2×

Product 1

HCID 22408759HCID 22408759, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4,4-Di-(t-butylperoxy)pentanohydrazide was prepared by reacting ethyl 4,4-di-(t-butylperoxy)pentanoate with 9 molar excess of 54% aqueous hydrazine. A 3-neck flask equipped with a magnetic stirrer, a thermometer and an addition funnel was charged with 125 mL of isopropanol (IPA), 15.3 g (0.05 mole) of 99% ethyl 4,4-di-(t-butylperoxy)pentanoate and 30 g (about 0.50 mole) of 54% aqueous hydrazine at 25° C. The solution was stirred for about 20 hours at 20°-25° C. Then the reaction mass was poured into 1000 mL of water and extracted once with 300 mL of methylene chloride. After drying over 10% by weight of anhydrous magnesium sulfate and separation of the spent desiccant by filtration, the methylene chloride was removed in vacuo leaving 14.4 g of liquid product. 30 mL of pentane were added and a solid was precipitated. The solid was separated by filtration and air dried, leaving 12.2 g (83.6% of theory, uncorrected) of a white solid having a melting point (mp) of 76°-78° C. An infrared (IR) spectrum of the product showed strong carbonyl absorption bands at 1640 cm-1 and at 1680 cm-1 and a strong NH band at 3300 cm-1. A DSC scan run on the product showed a peroxide decomposition exotherm at 170° C. These product data confirm that the product was 4,4-Di-(t-butylperoxy)pentanohydrazide (I-1).

Workup

  1. customA 3-neck flask equipped with a magnetic stirrer
  2. extractionextracted once with 300 mL of methylene chloride
  3. dry with materialAfter drying over 10% by weight of anhydrous magnesium sulfate and separation of the spent desiccant by filtration
  4. customthe methylene chloride was removed in vacuo

Sources & evidence

ORD record
ord-d50f19babe944c3ba4e8d61db4751f21
Source dataset
uspto-grants-1995_03
Patent number
US05399630

Reaction notes

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