Hydrochloric Acid → [2-(Methoxymethyl)phenyl]methanol

HRID 660795Notes

Reaction equation

HRID 660795 reaction equation
[C:1]1([CH2:9][OH:10])[C:2]([CH2:7][OH:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[H-].[Na+].I[CH3:14].Cl>CN(C=O)C.O.CCOC(C)=O>[CH3:14][O:8][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH2:9][OH:10]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 691531,2-Benzenedimethanol

Product 1

HCID 13681092[2-(Methoxymethyl)phenyl]methanol

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1,2-benzenedimethanol (1.38 g, 10 mmol) in DMF (10 mL) cooled in an ice bath is added NaH (400 mg, 60% in mineral oil, 10 mmol) in portions. The mixture is stirred at 0° C. for 15 min then at RT for 30 min. To this is added iodomethane (1.45 g, 10.2 mmol) dropwise and the mixture is stirred at RT for 1 h. Ice, EtOAc and water is added and the mixture is acidified with 1N HCl. The organic phase is washed with water and brine then is dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue purified by column chromatography using a gradient of 0-100% EtOAc/hexane as eluent to give the title compound.

Workup

  1. waitat RT for 30 min
  2. stirringthe mixture is stirred at RT for 1 h
  3. washThe organic phase is washed with water and brine
  4. dry with materialthen is dried over magnesium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-8f30465003434fd3b9bdcc2a7c4b1475
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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