Benzene → 3-Pentadecanone

HRID 1087764노트

반응식

HRID 1087764 반응식
[CH:1]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.ClN(Cl)C([O:17][CH2:18][CH3:19])=O.[CH:21]1C=CC=CC=1>CCOCC.CCCCCC>[CH3:21][CH2:19][C:18](=[O:17])[CH2:1][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH3:2]

참가 물질

6

반응물 3

HCID 241BenzeneHCID 15164Cyclododecene, (E)-HCID 26195N,N-Dichlorourethan

생성물 1

HCID 5459723-Pentadecanone

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8058Hexane용매

실험 절차

A solution of 15.7 g cyclododecene and 15.8 g dichlorourethane in 125 ml of benzene was refluxed for 12 hours under a nitrogen atmosphere. The reaction mixture was cooled, diluted with 100 ml of ether and then washed repeatedly with saturated sodiumbisulfite solution. After washing with brine the organic layer was dried and concentrated to give 19.5 g of crudechlorourethane. This was heated at 100°-120° C. for 6 hours. The resulting thick dark oil was diluted with hexane and allowed to stand in the freezer overnight. The solid was filtered and recrystallized from hexane/dichloromethane to give 5.66 g of white crystals, m.p. 84°-86° C. The mother liquor was concentrated to give 5.23 g of thick oil which after flash chromatography (silica gel; ethyl acetate/hexane) gave additional 1.23 g of white crystals, m.p. 85° C. and 0.96 g of a clear oil, which slowly solidified. Recrystallization from hexane gave 0.25 g of crystals, m.p. 72°-74° C.

후처리

  1. temperatureThe reaction mixture was cooled
  2. washwashed repeatedly with saturated sodiumbisulfite solution
  3. washAfter washing with brine the organic layer
  4. customwas dried
  5. concentrationconcentrated
  6. customto give 19.5 g of crudechlorourethane
  7. temperatureThis was heated at 100°-120° C. for 6 hours
  8. customto stand in the freezer overnight
  9. filtrationThe solid was filtered
  10. customrecrystallized from hexane/dichloromethane

출처 및 근거

ORD 기록
ord-b6cb2e7660d640d38d70191c56cf66e1
출처 데이터셋
uspto-grants-1990_10
특허 번호
US04960771

반응 노트

불러오는 중…