Methanol → 4-Hydroxy-1-phenylcyclohexane-1-carbonitrile

HRID 1580261ノート

反応式

HRID 1580261 の反応式
CO.[C:3]([C:5]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]1)#[N:4].[BH4-].[Na+]>O1CCCC1>[C:3]([C:5]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]1)#[N:4]

参加物

5

反応物 3

HCID 887MethanolHCID 912824-Oxo-1-phenylcyclohexanenitrileHCID 4311764Sodium borohydride

生成物 1

HCID 124536734-Hydroxy-1-phenylcyclohexane-1-carbonitrile収率 43.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To an ice and methanol cooled solution of 4 g. (0.0205 M) of 4-cyano-4-phenylcyclohexanone (a) (prepared as in J. Chem. Soc. 1959, 1446) in 150 ml. of tetrahydrofuran, a suspension of 1 g. of sodium borohydride in 50 ml. of tetrahydrofuran is added in 5 ml. portions in the course of about 10 minutes. The mixture is stirred for about 30 minutes and allowed to stand in the cold for about 18 hours. The bulk of the solvent is removed under vacuum and the residue treated with water. The precipitate is extracted with ether and the organic fraction washed successively with 2.5 N hydrochloric acid solution, saturated aqueous sodium bicarbonate, water and brine and then evaporated to dryness. The residue is recrystallized with benzene to give 1.81 g. (43.8% yield) of 4-cyano-4-phenylcyclohexanol (b) melting at 103° to 111° C.

後処理

  1. customin the course of about 10 minutes
  2. customcold for about 18 hours
  3. customThe bulk of the solvent is removed under vacuum
  4. additionthe residue treated with water
  5. extractionThe precipitate is extracted with ether
  6. washthe organic fraction washed successively with 2.5 N hydrochloric acid solution, saturated aqueous sodium bicarbonate, water and brine
  7. customevaporated to dryness
  8. customThe residue is recrystallized with benzene
  9. customto give 1.81 g

出典と根拠

ORDレコード
ord-53bd0334ae8d4ba8833f46f4d1df078e
出典データセット
uspto-grants-1976_01
特許番号
US03932425

反応ノート

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