Cyclopropanecarboxylic acid → n-Butyl cyclopropyl ketone

HRID 66407

반응식

HRID 66407 반응식
[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

참가 물질

4

반응물 2

HCID 15655Cyclopropanecarboxylic acidHCID 178418339Butyllithium

생성물 1

HCID 11029852n-Butyl cyclopropyl ketone

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

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 - 4N 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--).

후처리

  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)

출처 및 근거

ORD 기록
ord-8b0fdf1f53984ba8a92265806892d021
출처 데이터셋
uspto-grants-1978_12
특허 번호
US04131737

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