Water → Cyclohexanepentanol

HRID 530514Notes

Reaction equation

HRID 530514 reaction equation
[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

Participants

6

Reactant 4

HCID 962Water2×HCID 14797Potassium HydroxideHCID 94769Cyclohexanepentanoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 269450CyclohexanepentanolYield 88.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-96290f5f43514dcda205c5581e8785b7
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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