Cyclopropanecarboxylic acid → n-Butyl cyclopropyl ketone

HRID 1065162Notes

Reaction equation

HRID 1065162 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 mmoles) 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-4 N hydrochloric acid. The ethereal 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 : δ2.55 (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-ef0a3984e7904f6f903c5398b95c185c
Source dataset
uspto-grants-1982_05
Patent number
US04328358

Reaction notes

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