Toluene → 7-Oxo-5-octenoic acid methyl ester

HRID 1981222Notes

Reaction equation

HRID 1981222 reaction equation
C([CH:3]([CH2:8][CH3:9])[C:4]([O:6][CH3:7])=[O:5])=O.C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:17][C:18](=[O:20])[CH3:19])C=CC=CC=1.[C:33]1(C)C=CC=CC=1>>[CH3:7][O:6][C:4](=[O:5])[CH2:3][CH2:8][CH2:9][CH:33]=[CH:17][C:18](=[O:20])[CH3:19]

Participants

4

Reactant 3

HCID 1140TolueneHCID 150381-(Triphenylphosphoranylidene)acetoneHCID 15570303Methyl 2-formylbutanoate

Product 1

HCID 570595497-Oxo-5-octenoic acid methyl ester

Procedure

Methyl formylbutyrate (13 g) and 1-triphenylphosphoranylidene-2-propanone (31.4 g) were refluxed together in toluene (200 ml) for 30 minutes. The toluene was then evaporated off and ether (200 ml) added to the residue to give a suspension which was stirred at room temperature for 5 minutes. The suspended triphenylphosphine oxide was filtered off and washed with a further 100 ml of ether. The combined ether solutions were evaporated to dryness to give a yellow oil which was distilled at 0.1 mm Hg using a Kugelrohr apparatus (air bath temperature 140° C.) to yield 7-oxo-5-octenoic acid methyl ester as a colourless oil.

Workup

  1. customThe toluene was then evaporated off
  2. additionether (200 ml) added to the residue
  3. customto give a suspension which
  4. filtrationThe suspended triphenylphosphine oxide was filtered off
  5. washwashed with a further 100 ml of ether
  6. customThe combined ether solutions were evaporated to dryness
  7. customto give a yellow oil which
  8. distillationwas distilled at 0.1 mm Hg
  9. customa Kugelrohr apparatus (air bath temperature 140° C.)

Sources & evidence

ORD record
ord-ce739595dd96443b94ad8c7fab665b16
Source dataset
uspto-grants-1985_04
Patent number
US04513005

Reaction notes

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