Water → Methyl 5-formyl-2-propylpentanoate

HRID 325817Notes

Reaction equation

HRID 325817 reaction equation
O=[O+][O-].[CH2:4]([CH:7]([CH2:12][CH2:13][CH2:14][CH:15]=C)[C:8]([O:10][CH3:11])=[O:9])[CH2:5][CH3:6].CC[O:19]CC.O>C(O)(=O)C.[Zn]>[CH:15]([CH2:14][CH2:13][CH2:12][CH:7]([CH2:4][CH2:5][CH3:6])[C:8]([O:10][CH3:11])=[O:9])=[O:19]

Participants

7

Reactant 4

HCID 962WaterHCID 3283Diethyl Ether2×HCID 24823OzoneHCID 20462871Methyl 2-propyl-6-heptenoate

Product 1

HCID 20462876Methyl 5-formyl-2-propylpentanoate

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Ozone stream was bubled into a solution of methyl 2-propyl-6-heptenoate (2 g) in glacial acetic acid (80 ml) for 55 minutes at room temperature. Ether (100 ml) was added to the resulting mixture, followed by the portionwise addition of zinc powder (10 g) and water (1.1 ml) under cooling. The mixture was heated under reflux until KI-starch test became negative. After cooling, ether (100 ml) was added to the mixture, which was then filtered. The organic layer was separated, washed with water, dried and concentrated. The resulting residue was purified by silica gel column chromatography to give oil of methyl 5-formyl-2-propylpentanoate (1.1 g).

Workup

  1. temperatureunder cooling
  2. temperatureThe mixture was heated
  3. temperatureAfter cooling
  4. filtrationwas then filtered
  5. customThe organic layer was separated
  6. washwashed with water
  7. customdried
  8. concentrationconcentrated
  9. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d0a0313ccf6b4f3eb7d5ae436618247a
Source dataset
uspto-grants-1984_04
Patent number
US04443365

Reaction notes

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