Sulfuric Acid → (3-Methoxy-2-methylphenyl)methanol

HRID 1386412Notes

Reaction equation

HRID 1386412 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].OS(O)(=O)=O>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

5

Reactant 3

HCID 1118Sulfuric AcidHCID 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 1N H2SO4. 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 m/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-b5bb86064e1542d587f08c29f7d0d627
Source dataset
uspto-grants-2001_07
Patent number
US06265422B1

Reaction notes

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