Water → (4-Cyclohexylphenyl)methanol

HRID 530533

反応式

HRID 530533 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1([C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.O.[OH-].[K+]>CCOCC>[CH:7]1([C:13]2[CH:14]=[CH:15][C:16]([CH2:17][OH:18])=[CH:20][CH:21]=2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

参加物

6

反応物 4

HCID 962Water2 回HCID 14797Potassium HydroxideHCID 883374-Cyclohexylbenzoic acidHCID 21226445Aluminium lithium hydride

生成物 1

HCID 22492024(4-Cyclohexylphenyl)methanol収率 98.7%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
0 °C

実験手順

Under nitrogen atmosphere, at 0° C., to a stirring mixture of LiAlH4 (2.0 M THF solution, 5.3 mL, 10.53 mmol) in dry Et2O (10 mL), commercially available 4-cyclohexylbenzoic acid (0.5 g, 2.45 mmol) in dry Et2O (5.0 mL) was added dropwise. The mixture was left to react at rt for 4 h, then at 0° C. H2O (0.45 mL), 3.0 M KOH solution (0.45 mL) and H2O (2.0 mL) were very slowly added. The mixture was stirred for 1 h at 0° C., filtered to remove the solid residue, and the organic phase dried over Na2SO4. The organic solution was again filtered and concentrated to dryness affording the title compound (0.46 g, quant.), which was used in the next step without any further purification. 1H NMR (CDCl3): δ 8.05-7.94 (m, 2H), 7.35-7.23 (m, 2H), 4.39 (q, 2H, J=7.12 Hz), 2.59 (tt, 1H J=11.41, 3.27 Hz), 1.97-1.73 (m, 5H), 1.53-1.34 (m, 6H).

後処理

  1. additionwas added dropwise
  2. waitThe mixture was left
  3. customto react at rt for 4 h
  4. customat 0° C
  5. filtrationfiltered
  6. customto remove the solid residue
  7. dry with materialthe organic phase dried over Na2SO4
  8. filtrationThe organic solution was again filtered
  9. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-2467069b133d450c8711dba189212175
出典データセット
uspto-grants-2016_05
特許番号
US09353075B2

関連ノート

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