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

HRID 127560Notes

Reaction equation

HRID 127560 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-1e0f64dd05ae439ab604171cea519681
Source dataset
uspto-grants-1981_03
Patent number
US04256644

Reaction notes

Loading…