Water → HCID 68481936, compound

HRID 2361564Notes

Reaction equation

HRID 2361564 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][CH:8]1[CH:13]=[C:12]([CH3:14])[CH2:11][CH2:10][C:9]1([CH:17]=[CH2:18])[CH:15]=[O:16].O.[OH-].[Na+]>C(OCC)C>[CH3:7][CH:8]1[CH:13]=[C:12]([CH3:14])[CH2:11][CH2:10][C:9]1([CH2:15][OH:16])[CH:17]=[CH2:18]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 44542715HCID 44542715, compound

Product 1

HCID 68481936HCID 68481936, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of LiAlH4 (0.114 g, 30 mmol) in diethylether (20 ml) was added a solution of 2,4-dimethyl-1-vinylcyclohex-3-enecarbaldehyde (56 mmol) in diethylether (10 ml) at 5° C. The mixture was stirred at room temperature for 1 h. 0.1 ml of water, 0.1 ml 16% aq. NaOH and 0.3 ml of water were carefully added dropwise. The mixture was stirred for 2 h, was then filtered and concentrated in vacuo. The residue was purified by chromatography to give (2,4-dimethyl-1-vinylcyclohex-3-enyl)methanol (76% yield).

Workup

  1. stirringThe mixture was stirred for 2 h
  2. filtrationwas then filtered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-b55993212f8d4fb8b3b39328aa72c1b3
Source dataset
uspto-grants-2014_04
Patent number
US08691746B2

Reaction notes

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