Benzene → 3-Pentadecanone

HRID 1087764

反応式

HRID 1087764 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 5459723-Pentadecanone

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8058Hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b6cb2e7660d640d38d70191c56cf66e1
出典データセット
uspto-grants-1990_10
特許番号
US04960771

関連ノート

読み込み中…