Water → trans-3-Octen-1-ol

HRID 1470687

Reaction equation

HRID 1470687 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7](O)(=[O:15])[CH2:8]/[CH:9]=[CH:10]/[CH2:11][CH2:12][CH2:13][CH3:14].O.[OH-].[Na+]>C1COCC1>[CH2:7]([OH:15])[CH2:8]/[CH:9]=[CH:10]/[CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 5282716(E)-Oct-3-enoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 5364475trans-3-Octen-1-olYield 76.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiAlH4 (13.5 mL, 13.5 mmol, 1 M/THF) was added to an ice cold solution of (E)-oct-3-enoic acid (7-1, 1.86 g, 13.1 mmol) in THF (48 mL). The reaction was allowed to warm to room temperature and after 2 h, was cooled in an ice bath and 50 mL H2O was added slowly. NaOH (3 M, 50 mL) and H2O (50 mL) were added and the resulting mixture was extracted with dichloromethane (3×100 mL). The combined organic layer was washed with brine (100 mL) and was then dried (Na2SO4), filtered and evaporated. Purification of the residue by flash chromatography on silica gel (Isco Combiflash unit) gave the title compound (1.283 g, 76%).

Workup

  1. temperaturewas cooled in an ice bath
  2. extractionthe resulting mixture was extracted with dichloromethane (3×100 mL)
  3. washThe combined organic layer was washed with brine (100 mL)
  4. dry with materialwas then dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customPurification of the residue by flash chromatography on silica gel (Isco Combiflash unit)

Sources & evidence

ORD record
ord-85b4bd52aa6848f5bf8fa8c7e9ecf861
Source dataset
uspto-grants-2015_04
Patent number
US09006464B2

Linked notes

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