Butyl bromide → piperonyl butyl ether

HRID 2103741노트

반응식

HRID 2103741 반응식
[H-].[Na+].[CH2:3]([OH:13])[C:4]1[CH:12]=[CH:11][C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=1.Br[CH2:15][CH2:16][CH2:17][CH3:18]>O1CCCC1>[CH2:15]([O:13][CH2:3][C:4]1[CH:12]=[CH:11][C:10]2[O:9][CH2:8][O:7][C:6]=2[CH:5]=1)[CH2:16][CH2:17][CH3:18]

참가 물질

5

반응물 3

HCID 8002Butyl bromideHCID 10322Piperonyl alcoholHCID 24758Sodium hydride

생성물 1

HCID 10013282piperonyl butyl ether수율 38.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

4 g of sodium hydride (60%) and 100 ml of tetrahydrofuran (THF) were stirred in a nitrogen stream. Thereto was dropwise added, in 30 minutes, 15.2 g (0.1 mol) of piperonyl alcohol dissolved in 70 ml of THF, followed by stirring for 30 minutes. Thereto was dropwise added 13.7 g (0.1 mol) of 1-bromobutane dissolved in THF, followed by stirring for 12 hours. The stirring was stopped and the reaction mixture was concentrated. The concentrate was dropped into an excess amount of a 2 N aqueous hydrochloric acid solution. Heptane was added thereto for extraction. The extract was washed with water until the washings became neutral, and then concentrated. The concentrate was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to obtain 8.0 g of piperonyl butyl ether at a yield of 38.5% as a transparent oily substance.

후처리

  1. additionThereto was dropwise added, in 30 minutes
  2. stirringby stirring for 12 hours
  3. concentrationthe reaction mixture was concentrated
  4. additionThe concentrate was dropped into an excess amount of a 2 N aqueous hydrochloric acid solution
  5. additionHeptane was added
  6. extractionfor extraction
  7. washThe extract was washed with water until the washings
  8. concentrationconcentrated
  9. customThe concentrate was purified by silica gel column chromatography (hexane:ethyl acetate=30:1)

출처 및 근거

ORD 기록
ord-577e0c836b344dddb6a54d942031d1f8
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576125B2

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