Water → [4-(2-Methylpropyl)phenyl]methanol

HRID 1059064Notes

Reaction equation

HRID 1059064 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1)[CH:8]([CH3:10])[CH3:9].O.[OH-].[Na+]>C(OCC)C>[CH2:7]([C:11]1[CH:12]=[CH:13][C:14]([CH2:15][OH:16])=[CH:17][CH:18]=1)[CH:8]([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 577537Benzaldehyde, 4-(2-methylpropyl)-HCID 21226445Aluminium lithium hydride

Product 1

HCID 14620446[4-(2-Methylpropyl)phenyl]methanolYield 94.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Lithium aluminum hydride (586 mg, 15.4 mmol) was slurried in diethyl ether (50 mL) and cooled in an ice bath. A solution of 4-isobutylbenzaldehyde (5.00 g, 30.9 mmol) in diethyl ether (30 mL) was added dropwise over 10 min and the mixture was stirred for 30 min before successive addition of water (0.6 mL), 15% aq NaOH (0.6 mL), and water (1.8 mL). The resulting precipitate was removed via filtration and the filtrate was dried (MgSO4), filtered, and evaporated in vacuo to give 4-isobutylbenzyl alcohol (4.78 g, 94%). 1H NMR (CDCl3) 7.28 (d, 2H), 7.13 (d, 2H), 4.63 (s, 2H), 2.45 (d, 2H), 1.85 (m, 1H), 0.90 (d, 6H).

Workup

  1. temperaturecooled in an ice bath
  2. customThe resulting precipitate was removed via filtration
  3. dry with materialthe filtrate was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-b423a4880ba64afcb3cdb56abc1c0356
Source dataset
uspto-grants-2003_02
Patent number
US06518424B1

Reaction notes

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