Methyl 3-ethylbenzoate → (3-Ethylphenyl)methanol

HRID 2045838

Reaction equation

HRID 2045838 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=1)[C:12](OC)=[O:13])[CH3:8]>C1COCC1>[CH2:7]([C:9]1[CH:10]=[C:11]([CH2:12][OH:13])[CH:16]=[CH:17][CH:18]=1)[CH3:8]

Participants

4

Reactant 2

HCID 12430992Methyl 3-ethylbenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 104659(3-Ethylphenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (3.1 mL of 1.0 M solution in THF, 3.1 mmol) was added to a solution of methyl 3-ethylbenzoate (500 mg, 3.05 mmol) in THF (12 mL) at 0° C. After 2 h at 0° C., the reaction was quenched by the addition of saturated aqueous Rochelle's salt (50 mL) and stirred vigorously overnight at room temperature. The reaction mixture was extracted with Et2O (3×100 mL). The combined organic phase was dried (Na2SO4), filtered and concentrated in vacuo to afford (3-ethylphenyl)methanol which was shown to be ˜90% pure by 1H NMR analysis and was taken on without further purification.

Workup

  1. customthe reaction was quenched by the addition of saturated aqueous Rochelle's salt (50 mL)
  2. extractionThe reaction mixture was extracted with Et2O (3×100 mL)
  3. dry with materialThe combined organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e615c22f6a3f46d3b3c09d9f79bfbbb8
Source dataset
uspto-grants-2013_11
Patent number
US08592413B2

Linked notes

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