Water → 4-Neopentylbenzyl alcohol

HRID 1610708Notes

Reaction equation

HRID 1610708 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:12]1[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=1)[C:8]([CH3:11])([CH3:10])[CH3:9].O.[OH-].[Na+]>O1CCCC1>[CH2:7]([C:12]1[CH:20]=[CH:19][C:15]([CH2:16][OH:17])=[CH:14][CH:13]=1)[C:8]([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 81670894-(2,2-Dimethylpropyl)benzoic acidHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 574858764-Neopentylbenzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (1.13 g, 29.9 mmol) in tetrahydrofuran (50 ml) was added dropwise a solution of 4-neopentylbenzoic acid (3.830 g, 19.92 mmol) in tetrahydrofuran (30 ml) under ice-cooling, and the mixture was stirred overnight at room temperature. After ice-cooling the reaction solution, water (1 ml), a 15% aqueous sodium hydroxide solution (1 ml) and water (2.5 ml) were successively added dropwise to decompose excess lithium aluminum hydride. The mixture was stirred as it was at room temperature for 2 hrs. The resulting precipitate was removed by filtration, and the precipitate was washed with ethyl acetate. The solvent of the recovered filtrate was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=6/1−3/1) to give the objective substance.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred as it
  3. waitwas at room temperature for 2 hrs
  4. customThe resulting precipitate was removed by filtration
  5. washthe precipitate was washed with ethyl acetate
  6. customThe solvent of the recovered filtrate was evaporated under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=6/1−3/1)
  8. customto give the objective substance

Sources & evidence

ORD record
ord-6bf0de51e6e34089a1881ac6e34755da
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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