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

HRID 480286Notes

Reaction equation

HRID 480286 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) δ 7.26 (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-482c49719fdc4f3d9374f94c9ba7f24d
Source dataset
uspto-grants-2003_11
Patent number
US06649657B2

Reaction notes

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