4-Isobutylbenzoic acid → [4-(2-Methylpropyl)phenyl]methanol

HRID 1699006Notes

Reaction equation

HRID 1699006 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:11]1[CH:19]=[CH:18][C:14]([C:15](O)=[O:16])=[CH:13][CH:12]=1)[CH:8]([CH3:10])[CH3:9]>C1COCC1>[CH2:7]([C:11]1[CH:12]=[CH:13][C:14]([CH2:15][OH:16])=[CH:18][CH:19]=1)[CH:8]([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 381114-Isobutylbenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 14620446[4-(2-Methylpropyl)phenyl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium aluminum hydride (30 mL, 1M in THF, 30 mmol) was added dropwise to a solution of 4-isobutylbenzoic acid (5.34 g, 30 mmol) in THF (50 mL) at 0° C. The ice bath was removed and the reaction was stirred at room temperature for 1 h. The reaction was carefully poured onto a mixture of ice and aqueous HCl (10 mL, 6N). The product was extracted into EtOAc and the organic solution was dried (MgSO4), filtered, and concentrated to obtain (4-isobutyl-phenyl)-methanol which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ7.26 (d, 2H), 7.13 (d, 2H), 4.65 (s, 2H), 2.46 (d, 2H), 1.85 (m, 1H), 0.89 (d, 6H).

Workup

  1. customThe ice bath was removed
  2. additionThe reaction was carefully poured onto a mixture of ice and aqueous HCl (10 mL, 6N)
  3. extractionThe product was extracted into EtOAc
  4. dry with materialthe organic solution was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ffccd030cda04f65ae95f201f0c025b3
Source dataset
uspto-grants-2002_02
Patent number
US06344485B1

Reaction notes

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