Water → (2-Methoxy-6-methylphenyl)methanol

HRID 1946350Notes

Reaction equation

HRID 1946350 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[C:9]=1[C:10](OCC)=[O:11].O>C1COCC1.C(O)C>[CH3:7][C:8]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[C:9]=1[CH2:10][OH:11]

Participants

6

Reactant 3

HCID 962WaterHCID 5910602-Methoxy-6-methyl-benzoic acid ethyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 13208697(2-Methoxy-6-methylphenyl)methanolYield 97.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 1.0 M lithium aluminium hydride in anhydrous THF (3.6 ml, 3.6 mmol), under nitrogen, was added anhydrous THF (12 ml). Ethyl 2-methyl-6-(methyloxy)benzoate (1 g, 5.2 mmol, ABCR) in anhydrous THF (2 ml) was then added over 5 min with stirring. The solution was stirred for 15 min and then heated at gentle reflux for 100 min. The solution was allowed to cool. A 5% solution of water in ethanol was added dropwise. The solvent was removed in vacuo and acidified using 1 to 2M aqueous HCl. The mixture was extracted with chloroform and the organic solvent removed in vacuo to give the title compound as yellow solid (0.775 g); LCMS: (System 4) MH+=152, tRET=1.78 min.

Workup

  1. stirringThe solution was stirred for 15 min
  2. temperatureheated
  3. temperatureat gentle reflux for 100 min
  4. temperatureto cool
  5. customThe solvent was removed in vacuo
  6. extractionThe mixture was extracted with chloroform
  7. customthe organic solvent removed in vacuo

Sources & evidence

ORD record
ord-ba0961f93c3b4a95913b1d02460d84cf
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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