Water → (3-Tert-butylphenyl)methanol

HRID 1610746Notes

Reaction equation

HRID 1610746 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14](O)=[O:15])([CH3:10])([CH3:9])[CH3:8].O.[OH-].[Na+]>CCOCC>[C:7]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[CH2:14][OH:15])([CH3:10])([CH3:8])[CH3:9]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 139037m-tert-Butylbenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 19028489(3-Tert-butylphenyl)methanolYield 90%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension (40 ml) of lithium aluminum hydride (1.38 g, 36.2 mmol) in ether was added dropwise a solution of 3-tert-butylbenzoic acid (3.13 g, 17.6 mmol) in ether (40 ml) under ice-cooling, and the mixture was stirred at room temperature for 2 hrs. After completion of the reaction, water (1.38 ml), 15% aqueous sodium hydroxide solution (1.38 ml) and water (4.2 ml) were successively added dropwise slowly under ice-cooling. The obtained solid was filtered with celite, and washed with ethyl acetate. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1, 4:1) to give 3-tert-butylbenzyl alcohol (2.59 g, 90%) as a colorless transparent oil.

Workup

  1. temperaturecooling
  2. additionwere successively added dropwise slowly under ice-
  3. temperaturecooling
  4. filtrationThe obtained solid was filtered with celite
  5. washwashed with ethyl acetate
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1, 4:1)

Sources & evidence

ORD record
ord-5e70151ab46f48fdb451cbb8677b147f
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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