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

HRID 409378Notes

Reaction equation

HRID 409378 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) δ 1.13 (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-377a9bcdce1f40278731312af344e9ea
Source dataset
uspto-grants-2014_06
Patent number
US08759340B2

Reaction notes

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