Hydrochloric Acid → Neopentyl isobutyl ketone

HRID 2292473Notes

Reaction equation

HRID 2292473 reaction equation
[Mg].Cl[CH2:3][C:4]([CH3:7])([CH3:6])[CH3:5].BrCCBr.[C:12](Cl)(=O)[CH:13]([CH3:15])[CH3:14].Cl.C[CH2:20][O:21]CC>>[CH3:5][C:4]([CH3:7])([CH2:3][C:20](=[O:21])[CH2:12][CH:13]([CH3:15])[CH3:14])[CH3:6]

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether3×HCID 78391,2-DibromoethaneHCID 129561-Chloro-2,2-dimethylpropaneHCID 62325Isobutyryl chlorideHCID 5462224Magnesium

Product 1

HCID 546074Neopentyl isobutyl ketone

Procedure

Mix magnesium turnings (45 mg, 1.85 mmol) and 1-chloro-2,2-dimethylpropane (74.6 mg, 0.7 mmol) in anhydrous ether (9 mL). Heat and stir vigorously, then add, by dropwise addition, 1,2-dibromoethane (156 mg, 0.839 mmol) in anhydrous ether (1.5 mL). Reflux for 12 hours, place under an argon atmosphere and cool to 0°-5° C. Add, by dropwise addition, a solution of isobutyryl chloride (0.533 mmol) in anhydrous diethyl ether (1.5 mL). Stir at 0°-5° C. for 1.5 hours, pour into a mixture of ice and concentrated hydrochloric acid (0.15 mL) and separate the organic phase. Wash with ethyl acetate, 5% aqueous sodium carbonate and brine. Dry (MgSO4) and evaporate the solvent in vacuo to give 2,2,6-trimethyl-4-heptanone.

Workup

  1. temperatureHeat
  2. temperatureReflux for 12 hours
  3. temperatureplace under an argon atmosphere and cool to 0°-5° C
  4. additionAdd, by dropwise addition
  5. stirringStir at 0°-5° C. for 1.5 hours
  6. customseparate the organic phase
  7. washWash with ethyl acetate, 5% aqueous sodium carbonate and brine
  8. dry with materialDry (MgSO4)
  9. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-8fed585e60a74a75ae2cf4c1f065378c
Source dataset
uspto-grants-1997_11
Patent number
US05683982

Reaction notes

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