Hydrochloric Acid → (2,6-Dimethylphenyl)methanol

HRID 25019

Reaktionsgleichung

Reaktionsgleichung von HRID 25019
[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]

Komponenten

10

Edukt 5

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

Produkt 1

HCID 186748(2,6-Dimethylphenyl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4fec5f6ba13642538e68c81086401b1a
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858602B2

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