Sodium Bicarbonate → 6-Methyl-6-hepten-2-one

HRID 1448933Notes

Reaction equation

HRID 1448933 reaction equation
C1CO[C:3]([CH3:10])([CH2:4][CH2:5][CH2:6][C:7]([CH3:9])=[CH2:8])[O:2]1.C(=O)(O)[O-].[Na+]>CC(C)=O.Cl>[CH3:9][C:7]([CH2:6][CH2:5][CH2:4][C:3](=[O:2])[CH3:10])=[CH2:8]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 10975921HCID 10975921, compound

Product 1

HCID 1515096-Methyl-6-hepten-2-oneYield 70.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of 6,6-ethylenedioxy-2-methyl-hept-1-ene (12.2 g) in acetone (300 ml) and 10% hydrochloric acid (12 ml) is stirred at room temperature for 1.5 hours. The reaction is neutralized to pH 7 with a sodium bicarbonate solution and the resulting solids are filtered. The acetone is removed in vacuo and the residue is partitioned between ether and brine. The ether extract is dried (Na2SO4) and evaporated in vacuo to give 2-methyl-6-oxo-hept-1-ene as a pale yellow liquid (6.4 g), nmr (CDCl3,δ) 1.7 (br, s, CH3 --C=), 2.12 (s, CH3C=O), 2.4 (t, J=6 Hz, CH2C=O), 4.69 (br, s, 2H, H2C=C).

Workup

  1. filtrationthe resulting solids are filtered
  2. customThe acetone is removed in vacuo
  3. customthe residue is partitioned between ether and brine
  4. extractionThe ether extract
  5. dry with materialis dried (Na2SO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-9b42fc51efac4be69dd93e72bd6f11ad
Source dataset
uspto-grants-1980_02
Patent number
US04188328

Reaction notes

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