Hydrochloric Acid → (2,6-Dimethylphenyl)methanol

HRID 1986135Notes

Reaction equation

HRID 1986135 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4](O)=[O:5].C(=O)([O-])[O-].[K+].[K+].CI.[H-].[H-].[H-].[H-].[Li+].[Al+3].Cl>CN(C)C=O.C(OCC)(=O)C.O.C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[CH2:4][OH:5]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 124392,6-Dimethylbenzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 186748(2,6-Dimethylphenyl)methanol

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,6-dimethylbenzoic acid (10 g, 66.5 mmol) and potassium carbonate (9.18 g, 66.5 mmol) in dimethylformamide (67 ml), was added methyl iodide (8.28 ml, 133.16 mmol) in an ice bath, and the mixture was stirred for 16 hours. To the reaction mixture was added toluene and water, and the organic layer was washed with 3% K2CO3, 1N HCl, and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The oily residue was redissolved in dry THF (135 ml), added to LiAlH4 (3.79 g, 99.8 mmol), and stirred for 4 hours in an ice bath. To the reaction mixture was added 1N HCl slowly followed by ethyl acetate, and the organic layer was washed with brine, dried over Na2SO4, filtered and concentrated. The oily residue was used without further purification.

Workup

  1. washthe organic layer was washed with 3% K2CO3, 1N HCl, and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe oily residue was redissolved in dry THF (135 ml)
  6. stirringstirred for 4 hours in an ice bath
  7. washthe organic layer was washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe oily residue was used without further purification

Sources & evidence

ORD record
ord-e85a7e94541c4f5e8c1e0841b1018f91
Source dataset
uspto-grants-2009_06
Patent number
US07547802B2

Reaction notes

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