Tetrahydrofuran → 4-Phenylcyclohexanol

HRID 1259466

反応式

HRID 1259466 の反応式
[C:1]1([CH:7]([CH2:12][CH3:13])[CH2:8][C:9](=O)[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:20]1CCCC1>>[C:1]1([CH:7]2[CH2:12][CH2:13][CH:10]([OH:20])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

4

反応物 3

HCID 8028TetrahydrofuranHCID 109975814-Phenyl-2-hexanoneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 794974-Phenylcyclohexanol収率 74%

実験手順

4-Phenylhexanone (1.74 g; 10 mmoL) is mixed with 1M lithium aluminum hydride (LiAlH4) solution in tetrahydrofuran (THF) (10 mL; 10 mmoL). The reaction mixture is stirred and refluxed for 6 hrs. After the starting ketone is consumed as determined by thin-layer chromatography (TLC) and gas phase chromatography (GC), the reaction mixture is carefully quenched with water (40 mL) whereupon a precipitate forms. Then, hydrochloric acid (10 mL) is added to dissolve the precipitate, and the solution is twice extracted with diethyl ether (20 mL twice). The combined ether portions are dried with Na2SO4, and the solvent is evaporated to yield 4-phenylcyclohexanol (1.71 g; 74%). The purity and identity of the compound are established by TLC and GC using an authentic sample of the material obtained from Lancaster Company.

後処理

  1. temperaturerefluxed for 6 hrs
  2. customAfter the starting ketone is consumed
  3. customthe reaction mixture is carefully quenched with water (40 mL) whereupon a precipitate forms
  4. additionThen, hydrochloric acid (10 mL) is added
  5. dissolutionto dissolve the precipitate
  6. extractionthe solution is twice extracted with diethyl ether (20 mL twice)
  7. dry with materialThe combined ether portions are dried with Na2SO4
  8. customthe solvent is evaporated

出典と根拠

ORDレコード
ord-6f98873caa434d8a892634eccfcbb418
出典データセット
uspto-grants-2013_06
特許番号
US08466306B2

関連ノート

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