Carbon Dioxide → 16282-50-1

HRID 2164066Notes

Reaction equation

HRID 2164066 reaction equation
ClCC([O:5][CH2:6][CH3:7])=O.[CH3:8][C:9]([CH3:12])([O-])C.[K+].O1[CH2:16][CH2:15]1.[C:17](=O)=O.[C:20](O)([CH3:23])([CH3:22])C>>[CH:12]1([CH:7]([C:16]2[CH:15]=[CH:23][CH:20]=[CH:22][CH:17]=2)[CH:6]=[O:5])[CH2:9][CH2:8]1

Participants

6

Reactant 5

HCID 280Carbon DioxideHCID 6354Ethylene OxideHCID 6386tert-ButanolHCID 7751Ethyl chloroacetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 1487126216282-50-1

Procedure

In reaction scheme 1, the ketone is first reacted with ethyl chloroacetate under the conditions of the Darzens reaction in the presence of a strong base, for example potassium tertiary butoxide in tertiary butanol. The resulting stable oxirane intermediate is then saponified with base to give an unstable intermediate acid which rearranges, with loss of carbon dioxide, to form an α-cyclopropyl-phenyl acetaldehyde. This aldehyde is subsequently oxidised with a reagent known to be suitable for oxidising aldehyde groups to acids groups, for example moist silver oxide.

Workup

  1. customIn reaction scheme 1
  2. customto give an unstable intermediate acid which

Sources & evidence

ORD record
ord-588f91676f6343d5a7f06e0bfce9e7fa
Source dataset
uspto-grants-1979_01
Patent number
US04137324

Reaction notes

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