Water → HCID 22408733, compound

HRID 1031996Notes

Reaction equation

HRID 1031996 reaction equation
[C:1]([O:5][O:6][C:7]([O:15][O:16][C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:14])[CH2:8][C:9](OCC)=[O:10])([CH3:4])([CH3:3])[CH3:2].[NH2:21][NH2:22].CC(O)C.O>CCCCC>[C:1]([O:5][O:6][C:7]([O:15][O:16][C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:14])[CH2:8][C:9]([NH:21][NH2:22])=[O:10])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 9321Hydrazine2×HCID 108769Butanoic acid, 3,3-bis[(1,1-dimethylethyl)dioxy]-, ethyl ester2×

Product 1

HCID 22408733HCID 22408733, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Conditions

Temperature
0 °C

Procedure

3,3-Di-(t-butylperoxy)butanohydrazide was prepared by reacting ethyl 3,3-di-(t-butylperoxy)butanoate 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 100 mL of IPA, 14.6 g (0.05 mole) of 100% ethyl 3,3-di-(t-butylperoxy)butanoate and 30 g (about 0.50 mole) of 54% aqueous hydrazine at 25° C. The solution was stirred for about 20 hours at 20°-22° C., then the reaction mass was poured into 1000 mL of water and extracted twice with 200 mL portions 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 14.3 g (>100% of theory, uncorrected) of a liquid product. 75 mL of pentane was added, the solution cooled to 0° C. and a solid precipitated. The solid was separated by filtration nd air dried, leaving 4.8 g (35% of theory, uncorrected) of a white solid, mp, 62°-63° C.

Workup

  1. customA 3-neck flask equipped with a magnetic stirrer
  2. extractionextracted twice with 200 mL portions 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
  5. customleaving 14.3 g (>100% of theory, uncorrected) of a liquid product
  6. customa solid precipitated
  7. customThe solid was separated by filtration nd air
  8. customdried
  9. customleaving 4.8 g (35% of theory, uncorrected) of a white solid, mp, 62°-63° C.

Sources & evidence

ORD record
ord-f58fba40255a4e1cb74f821a88f22965
Source dataset
uspto-grants-1990_09
Patent number
US04956416

Reaction notes

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