Potassium Hydroxide → Trans 3-Acetyl-2,2-dimethylcyclopropane-1-carboxylic acid

HRID 1577798Notes

Reaction equation

HRID 1577798 reaction equation
[C:1]([CH:4]1[CH:6]([C:7]([O:9]CC)=[O:8])[C:5]1([CH3:13])[CH3:12])(=[O:3])[CH3:2].[OH-].[K+]>C(O)C>[C:1]([C@H:4]1[C@H:6]([C:7]([OH:9])=[O:8])[C:5]1([CH3:13])[CH3:12])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 12851673Ethyl 3-acetyl-2,2-dimethylcyclopropane-1-carboxylate

Product 1

HCID 67945237Trans 3-Acetyl-2,2-dimethylcyclopropane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-acetyl-2,2-dimethylcyclopropane-1-carboxylate (36.0 g, 0.2 m) and N potassium hydroxide (391 ml) in ethanol (391 ml) was refluxed for two hours. Excess alcohol was removed in vacuo and the resulting solution acidified with concentrated hydrochloric acid (≈40 ml). This precipitated a solid which was extracted with ether (3×200 ml), the ether dried over anhydrous MgSO4 and evaporated in vacuo to give a cream solid m.p. 111° C.

Workup

  1. customExcess alcohol was removed in vacuo
  2. customThis precipitated a solid which
  3. extractionwas extracted with ether (3×200 ml)
  4. dry with materialthe ether dried over anhydrous MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-49be5e1ce7ef44e1958870fb7529f8e7
Source dataset
uspto-grants-1981_09
Patent number
US04289711

Reaction notes

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