Water → 5-Phenyl-1-pentanol

HRID 530500Notes

Reaction equation

HRID 530500 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([CH2:13][CH2:14][CH2:15][CH2:16][C:17](O)=[O:18])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.[OH-].[K+]>CCOCC>[C:7]1([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14797Potassium HydroxideHCID 16757Benzenepentanoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 615235-Phenyl-1-pentanolYield 95.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

Under nitrogen atmosphere, at 0° C., to a stirring mixture of LiAlH4 (0.84 g, 22.44 mmol) in dry Et2O (55 mL), 5-phenylpentanoic acid (1.00 g, 5.61 mmol) in dry Et2O (10 mL) was added dropwise. The mixture was left to react at rt for 4 h, then at 0° C. H2O (0.85 mL), 3M KOH solution (0.85 mL) and H2O (2.85 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 (0.881 g, 95%) as a colorless oil. 1H NMR (CDCl3): δ 1.36-1.46 (m, 2H), 1.54-1.72 (m, 5H), 2.58-2.71 (m, 2H), 3.59-3.71 (m, 2H), 7.14-7.33 (m, 5H).

Workup

  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

Sources & evidence

ORD record
ord-4fff1bbe7c0641b1a0cbf977d7653811
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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