Hydrochloric Acid → 4,4-Dimethylhexanal

HRID 1441040Notes

Reaction equation

HRID 1441040 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][C:12]([CH3:19])([CH2:17][CH3:18])[CH2:13][CH2:14][C:15]#N.[OH2:20].Cl>C(OCC)C.O1CCOCC1>[CH3:11][C:12]([CH3:19])([CH2:17][CH3:18])[CH2:13][CH2:14][CH:15]=[O:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 224210484,4-Dimethylhexanenitrile

Product 1

HCID 222184,4-Dimethylhexanal

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

Diisobutylaluminium hydride (1M solution in toluene, 18.5 ml.) was added to a solution of 4,4-dimethylhexanenitrile (2.0 g.) in dry diethyl ether (100 ml.) stirred under nitrogen. The mixture was refluxed for 3 hours and cooled. A solution of water (2 ml.) and dioxane (10 ml.) was added dropwise followed by dilute hydrochloric acid (80 ml.) and the solution stirred for 1 hour. Diethyl ether was added and the ethereal extracts separated. The ethereal extracts were dried (anhydrous magnesium sulphate) and evaporated to give 4,4-dimethylhexanal (1.3 g.). Nuclear Magnetic Resonance Spectrum (NMR) was as follows: 0.9,6H,s; 1.4,7H,m; 2.4,2H,m; 9.7,1H,t.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. temperaturecooled
  3. stirringthe solution stirred for 1 hour
  4. customthe ethereal extracts separated
  5. dry with materialThe ethereal extracts were dried (anhydrous magnesium sulphate)
  6. customevaporated

Sources & evidence

ORD record
ord-c80523a9f8b84001a436544263e318e9
Source dataset
uspto-grants-1996_03
Patent number
US05502073

Reaction notes

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