Cyclopropanecarboxylic acid → n-Butyl cyclopropyl ketone

HRID 1706067Notes

Reaction equation

HRID 1706067 reaction equation
[CH:1]1([C:4]([OH:6])=O)[CH2:3][CH2:2]1.[CH2:7]([Li])[CH2:8][CH2:9][CH3:10]>CCOCC>[CH:1]1([C:4]([CH2:7][CH2:8][CH2:9][CH3:10])=[O:6])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 15655Cyclopropanecarboxylic acidHCID 178418339Butyllithium

Product 1

HCID 11029852n-Butyl cyclopropyl ketone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a vigorously-stirred solution of 31.0 g of cyclopropanecarboxylic acid in 330 ml of ether is added a solution of n-butyllithium (748 moles) in ca. 750 ml. of 2:1 ether-hexane during 1 hour at 5°-10° C. The resulting suspension is diluted with 300 ml of ether and stirred at room temperature for 2 hours and at reflux for 2 hours. The mixture is cooled and poured into several portions of 1:1 ice-4N hydrochloric acid. The etheral phases are combined and washed with brine, sodium carbonate solution, and brine. The extract is dried over magnesium sulfate and concentrated. The residue is distilled to provide a liquid, b.p. 102°-104° C. (80 mm), pmr spectrum (CDCl3): ∫2.55 (triplet, -CH2CO--).

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureThe mixture is cooled
  3. washwashed with brine, sodium carbonate solution, and brine
  4. dry with materialThe extract is dried over magnesium sulfate
  5. concentrationconcentrated
  6. distillationThe residue is distilled
  7. customto provide a liquid, b.p. 102°-104° C. (80 mm), pmr spectrum (CDCl3)

Sources & evidence

ORD record
ord-f9e1e074a4c142a591f81ec2cbd3b52d
Source dataset
uspto-grants-1980_06
Patent number
US04206151

Reaction notes

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