Aluminium lithium hydride → (2,4-Diethylphenyl)methanol

HRID 1186073Notes

Reaction equation

HRID 1186073 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:9]1[CH:18]=[C:17]([CH2:19][CH3:20])[CH:16]=[CH:15][C:10]=1[C:11](OC)=[O:12])[CH3:8]>C1COCC1>[CH2:7]([C:9]1[CH:18]=[C:17]([CH2:19][CH3:20])[CH:16]=[CH:15][C:10]=1[CH2:11][OH:12])[CH3:8]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66741803Methyl 2,4-diethylbenzoate

Product 1

HCID 21414896(2,4-Diethylphenyl)methanolYield 101.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (0.47 g, 11.8 mmol) in anhydrous THF (20 mL) at room temperature under nitrogen was added a solution of methyl 2,4-diethylbenzoate (1.5 g, 7.8 mmol) in THF (15 mL) with stirring over a period of −5 min. The resulting mixture was stirred at room temperature for 60 min and was then quenched by slow addition of ethyl acetate (until bubbling stopped). The mixture was partitioned between ethyl acetate and 1N HCl (aq). The aqueous layer was separated and extracted with ethyl acetate. Organic layers were combined, dried (MgSO4), and evaporated to dryness to give 1.3 g of the desired alcohol as a clear oil (yield of 100%). 1H NMR (300 MHz, CDCl3) δ1.13 (t, 3H), 1.17 (t, 3H), 2.58 (q, 2H), 2.61 (q, 2H), 4.43 (d, 2H), 5.02 (t, 1H), 7.05-7.11 (m, 3H).

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 60 min
  2. customwas then quenched by slow addition of ethyl acetate (until bubbling stopped)
  3. customThe mixture was partitioned between ethyl acetate and 1N HCl (aq)
  4. customThe aqueous layer was separated
  5. extractionextracted with ethyl acetate
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-c92bbfb0505e4ea1a4e9f9317ff3892b
Source dataset
uspto-grants-2014_03
Patent number
US08673897B2

Reaction notes

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