Water → Benzeneheptanol

HRID 530497Notes

Reaction equation

HRID 530497 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19](O)=[O:20])[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][CH2:18][CH2:19][OH:20])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14797Potassium HydroxideHCID 5209877-Phenylheptanoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 154271BenzeneheptanolYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

Under nitrogen atmosphere, at 0° C., to a stirring mixture of LiAlH4 (0.51 g, 13.57 mmol) in dry Et2O (35 mL), 7-phenylheptanoic acid (0.7 g, 3.39 mmol) in dry Et2O (5 mL) was dropwise added. The mixture was left to react at rt for 4 h, then at 0° C. H2O (0.51 mL), 3M KOH solution (0.51 mL) and H2O (1.70 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 (0.586 g, 90%) as a colorless oil. 1H NMR (CDCl3): δ 1.17-1.27 (m, 1H), 1.34-1.43 (m, 6H), 1.53-1.71 (m, 4H), 2.59-2.67 (m, 2H), 3.66 (t, J=6.5 Hz, 2H), 7.16-7.23 (m, 3H), 7.26-7.34 (m, 2H).

Workup

  1. additionwas dropwise added
  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-818019ceb0684ec0a6efca142153d3d4
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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