Water → HCID 123739102, compound

HRID 2273387Notes

Reaction equation

HRID 2273387 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8](=[CH:11][CH:12]([CH3:18])[CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])[CH:9]=[O:10].O.[OH-].[Na+]>C1COCC1>[CH3:7][C:8](=[CH:11][CH:12]([CH3:18])[CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])[CH2:9][OH:10]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 540823182,4,7-Trimethylocta-2,6-dienal

Product 1

HCID 123739102HCID 123739102, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LiAlH4 (4.8 g, 126 mmol) in THF (100 ml) was added dropwise a solution of 2,4,7-trimethylocta-2,6-dienal (20 g, 114 mmol) in THF (60 ml) at 5° C. over 1 h. The mixture was stirred at room temperature for 1 h. 5 ml of water, 5 ml of 15% aq. NaOH and 15 ml of water were carefully added subsequently. The mixture was stirred for 1 h. Precipitates were filtered and the filtrate was concentrated in vacuo. The residue was Kugelrohr-distilled to give 2,4,7-trimethylocta-2,6-dien-1-ol (98%). bp: 82-83° C./1 mbar.

Workup

  1. stirringThe mixture was stirred for 1 h
  2. customPrecipitates
  3. filtrationwere filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. distillationThe residue was Kugelrohr-distilled

Sources & evidence

ORD record
ord-9e297fd3cf6346ce96ffcf423daab946
Source dataset
uspto-grants-2015_09
Patent number
US09120994B2

Reaction notes

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