Methyl 3-methoxy-2-methylbenzoate → (3-Methoxy-2-methylphenyl)methanol

HRID 1859817Notes

Reaction equation

HRID 1859817 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[C:10]([CH3:19])=[C:11]([CH:16]=[CH:17][CH:18]=1)[C:12](OC)=[O:13]>C1COCC1>[CH3:7][O:8][C:9]1[C:10]([CH3:19])=[C:11]([CH2:12][OH:13])[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 12527049Methyl 3-methoxy-2-methylbenzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 15578709(3-Methoxy-2-methylphenyl)methanolYield 95.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 4.5 g (0.118 mol) of lithium aluminum hydride in 100 mL of THF was treated dropwise with a solution of 14.22 g (78.9 mmol) of methyl 3-methoxy-2-methylbenzoate in 120 mL of THF. The mixture was heated at reflux for 2.5 hours, then cautiously decomposed with 1NH2SO4. The mixture was extracted with EtOAc, and the EtOAc washed with dilute HCl, H2O, saturated NaHCO3, and saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure left 11.5 g (95.8% yield) of the product as a tan solid, mp 63-64° C. The structure was confirmed by NMR and mass spectroscopy MS n/z 153 (M+H+).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2.5 hours
  3. extractionThe mixture was extracted with EtOAc
  4. washthe EtOAc washed with dilute HCl, H2O, saturated NaHCO3, and saturated NaCl
  5. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-177989611ddc4d7580740202dd656537
Source dataset
uspto-grants-2003_03
Patent number
US06528535B2

Reaction notes

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