Sodium Hydroxide → 4-Phenyl-4-piperidinocyclohexanone

HRID 543462ノート

反応式

HRID 543462 の反応式
[C:1]1([C:7]2([N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)(=O)C.O.[O-2].[O-2].[O-2].[Cr+6]>[C:1]1([C:7]2([N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:8][CH2:9][C:10](=[O:13])[CH2:11][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

6

反応物 2

HCID 14798Sodium HydroxideHCID 1621714-Phenyl-4-piperidinocyclohexanol

生成物 1

HCID 133067564-Phenyl-4-piperidinocyclohexanone収率 93%

試薬・触媒・溶媒 3

HCID 10219390chromium (VI) trioxide触媒HCID 176Acetic Acid溶媒2 回HCID 962Water溶媒

実験手順

4-Phenyl-4-piperidinocyclohexanol (1.2 g, 4.6 mmoles) was dissolved in 50 ml of glacial acetic acid. The solution was cooled with an external ice-bath. Chromium trioxide (1 g, 10 mmole) was dissolved in 10 ml of water and 15 ml of glacial acetic acid, and was slowly added to the solution. After completion, the solution was stirred at room temperature for 4 hours. TLC analysis indicated no starting material was left. The solution was cooled with an ice-bath and was carefully made basic with sodium hydroxide solution. The greenish solution was extracted with 5×60 ml of ethyl ether. The combined ethereal solutions were dried over sodium sulfate and were concentrated under reduced pressure to give a white solid residue. Recrystallization from hexane gave 1.1 g of slightly brown crystalline solid (mp: 116°-117° C.) in 93% yield.

後処理

  1. temperatureThe solution was cooled with an external ice-bath
  2. waitwas left
  3. temperatureThe solution was cooled with an ice-bath
  4. extractionThe greenish solution was extracted with 5×60 ml of ethyl ether
  5. dry with materialThe combined ethereal solutions were dried over sodium sulfate
  6. concentrationwere concentrated under reduced pressure
  7. customto give a white solid residue
  8. customRecrystallization from hexane

出典と根拠

ORDレコード
ord-495d0cf6ea214ae9838786e35fd84560
出典データセット
uspto-grants-1984_05
特許番号
US04446065

反応ノート

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