Water → Cyclohexanepentanol

HRID 530514노트

반응식

HRID 530514 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1([CH2:13][CH2:14][CH2:15][CH2:16][C:17](O)=[O:18])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.O.[OH-].[K+]>CCOCC>[CH:7]1([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

참가 물질

6

반응물 4

HCID 962Water2회HCID 14797Potassium HydroxideHCID 94769Cyclohexanepentanoic acidHCID 21226445Aluminium lithium hydride

생성물 1

HCID 269450Cyclohexanepentanol수율 88.3%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매3회

반응 조건

온도
0 °C

실험 절차

Under nitrogen atmosphere, at 0° C., to a stirring mixture of 2M LiAlH4 (13.04 mL, 26.08 mmol) solution in Et2O in dry Et2O (67 mL), 5-cyclohexylpentanoic acid (1.2 g, 6.52 mmol) in dry Et2O (2 mL) was added dropwise. The mixture was left to react at rt for 4 h, then upon full conversion of the starting material, at 0° C., H2O (13.04 mL), 3M KOH (13.04 mL) solution and H2O (43.65 mL) were very slowly added. The mixture was stirred for 1 h at 0° C., filtered to remove the solid residue, and the remaining organic phase dried over Na2SO4. The organic solution was again filtered and concentrated to dryness affording the title compound (0.98 g, 88%) as a colorless oil. 1H NMR (DMSO-d6): δ 0.77-0.93 (m, 2H), 1.06-1.34 (m, 10H), 1.35-1.47 (m, 2H), 1.56-1.76 (m, 5H), 3.37 (t, J=6.6 Hz, 2H).

후처리

  1. waitThe mixture was left
  2. customto react at rt for 4 h
  3. filtrationfiltered
  4. customto remove the solid residue
  5. dry with materialthe remaining organic phase dried over Na2SO4
  6. filtrationThe organic solution was again filtered
  7. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-96290f5f43514dcda205c5581e8785b7
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353075B2

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