Hydrochloric Acid → 4-Methoxy-2,6-dimethylphenol

HRID 1733803Notes

Reaction equation

HRID 1733803 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([OH:9])[CH:6]=[C:5]([CH3:10])[C:3]=1[OH:4].[OH-].[Na+].[CH3:13]I.Cl>[Br-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl.O.C(Cl)Cl.O>[CH3:1][C:2]1[CH:8]=[C:7]([O:9][CH3:13])[CH:6]=[C:5]([CH3:10])[C:3]=1[OH:4]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 695602,6-Dimethylhydroquinone

Product 1

HCID 739964-Methoxy-2,6-dimethylphenolYield 70.3%

Reagents, catalysts & solvents 4

HCID 165294Benzyltriethylammonium bromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 21908982Water methylene chlorideSolvent

Procedure

A mixture of 10 mL of CH2Cl2, 10 mL of H2O, 460 mg of 2,6-dimethylhydroquinone, 200 mg of NaOH, 940 mg (2 eq) of methyl iodide, and 760 mg of benzyl triethyl ammonium bromide in CH2Cl2 /H2O (C) were stirred at room temperature under argon for 12 hr. Dilute HCl was added to adjust the pH to 7.0, followed by 200 mL of CH2Cl2, and the organic layer was extracted with brine (5×100 mL), dried over Na2SO4, the solvent evaporated under reduced pressure, and the crude product was applied to silica gel (230-400 mesh, CH2Cl2) to yield 356 mg of product 25, about 70% yield.

Workup

  1. extractionthe organic layer was extracted with brine (5×100 mL)
  2. dry with materialdried over Na2SO4
  3. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-4b933998241243d98b1120b3ecc8e71a
Source dataset
uspto-grants-1996_07
Patent number
US05532138

Reaction notes

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