Water → (4-Cyclohexylphenyl)methanol

HRID 530533

반응식

HRID 530533 반응식
[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

참가 물질

6

반응물 4

HCID 962Water2회HCID 14797Potassium HydroxideHCID 883374-Cyclohexylbenzoic acidHCID 21226445Aluminium lithium hydride

생성물 1

HCID 22492024(4-Cyclohexylphenyl)methanol수율 98.7%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2467069b133d450c8711dba189212175
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353075B2

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