Water → HCID 53414329, compound

HRID 1610738Notes

Reaction equation

HRID 1610738 reaction equation
[CH2:1]([O:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10](OC)=[O:11])[C:2]([CH3:5])([CH3:4])[CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH2:1]([O:6][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=1)[CH2:10][OH:11])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22261544HCID 22261544, compound

Product 1

HCID 53414329HCID 53414329, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(neopentyloxy)benzoate (4.51 g, 20.3 mmol) in tetrahydrofuran (100 ml) was added lithium aluminum hydride (1.93 g, 50.75 mmol) by small portions under ice-cooling, and the mixture was stirred at room temperature for 2 hrs. To the mixture were successively added slowly water (2 ml), 15% aqueous sodium hydroxide solution (2 ml) and water (6 ml) under ice-cooling. The obtained solid was filtered with celite, washed thoroughly with ethyl acetate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to give 3-(neopentyloxy)benzyl alcohol (3.81 g, 97%) as a colorless transparent oil.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. filtrationThe obtained solid was filtered with celite
  4. washwashed thoroughly with ethyl acetate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-f40061aefb84461e987a5ce23ee3a89b
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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