Sulfuric Acid → 6,6-Dimethylhepta-2,4-dienal

HRID 851168Notes

Reaction equation

HRID 851168 reaction equation
C[O:2][CH:3]=[CH:4][C:5]#[CH:6].[C:7]([Mg]Br)([CH3:10])([CH3:9])[CH3:8].[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH4+].[Cl-].OS(O)(=O)=O.O1CCC[CH2:27]1>C(O)C>[CH3:8][C:7]([CH3:10])([CH3:27])[CH:9]=[CH:2][CH:3]=[CH:4][CH:5]=[O:6]

Participants

8

Reactant 6

HCID 1118Sulfuric AcidHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 979831-Buten-3-yne, 1-methoxy-HCID 21226445Aluminium lithium hydrideHCID 178418586HCID 178418586, compound

Product 1

HCID 545330256,6-Dimethylhepta-2,4-dienal

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Freshly distilled 4-methoxy-but-3-en-1-yne is added dropwise under cooling to a solution of t-butyl-magnesium bromide in absolute tetrahydrofuran and the mixture stirred for 45 minutes at room temperature. The reaction mixture is first mixed with 13.6 g of ethanol, then, under cooling and inert gas atmosphere, reacted with 5.9 g of LiAlH4 and stirred overnight at room temperature. It is then mixed with saturated aqueous NH4Cl under cooling, acidified with H2SO4 and extracted with ether. The pure product is obtained by vacuum distillation b.p. (bulb tube) 50°/0.26 mbar.

Workup

  1. temperatureunder cooling
  2. stirringstirred overnight at room temperature
  3. temperatureunder cooling
  4. extractionextracted with ether
  5. customThe pure product is obtained by vacuum distillation b.p
  6. custom(bulb tube) 50°/0.26 mbar

Sources & evidence

ORD record
ord-c5a68c4760de42b388f6b92b21bc938b
Source dataset
uspto-grants-1983_05
Patent number
US04382951

Reaction notes

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