tert-BUTYL CHLORIDE → 2,2,4,4-Tetramethyl-3-pentanone Imine

HRID 648341Notes

Reaction equation

HRID 648341 reaction equation
[C:1](#[N:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[C:7](Cl)([CH3:10])([CH3:9])[CH3:8].[Na]>CCCCCC.O1CCCC1.O.CO.ClC1C=CC=CC=1>[C:2]([C:1](=[NH:6])[C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:5])([CH3:4])[CH3:3]

Participants

9

Reactant 3

HCID 10486tert-BUTYL CHLORIDEHCID 12416PivalonitrileHCID 5360545Sodium

Product 1

HCID 27556322,2,4,4-Tetramethyl-3-pentanone Imine

Reagents, catalysts & solvents 5

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 7964ChlorobenzeneSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

This was prepared by the method of J. Chem. Soc., Perkin I, 2087 (1976); ibid, 1797 (1974). Pivalonitrile (33.2 g.) and t-butyl chloride (44.4 g.) were added under nitrogen to a well stirred suspension of sodium sand (18.4 g.) in a mixture of hexane (80 ml.), tetrahydrofuran (20 ml.) and methanol (1 ml.) over one hour at 15°-20° C. The mixture was stirred three hours, a solution of chlorobenzene (2 g.) in tetrahydrofuran (5 ml.) added dropwise over 10 minutes and stirring continued for one hour. Methanol (20 ml.) was added with caution over 0.5 hr. followed by water until phases separated. The aqueous phase was extracted with ether and the combined organic phases dried and evaporated in vacuo. The residue was distilled to afford di-t-butylketone imine, b.p. 62°-63° C./19 mm.

Workup

  1. customThis was prepared by the method of J
  2. stirringThe mixture was stirred three hours
  3. stirringstirring
  4. customseparated
  5. extractionThe aqueous phase was extracted with ether
  6. customthe combined organic phases dried
  7. customevaporated in vacuo
  8. distillationThe residue was distilled

Sources & evidence

ORD record
ord-7ff32c0d88e5424eb347aaa61e72687e
Source dataset
uspto-grants-1983_10
Patent number
US04411925

Reaction notes

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