Water → 2,6-Diethylbenzene-1,4-diol

HRID 2103046Notes

Reaction equation

HRID 2103046 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].[CH2:12]([C:14]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][CH3:22])[C:15]=1N)[CH3:13].S(=O)(=O)(O)[OH:24].S(S([O-])=O)([O-])=O.[Na+].[Na+].[OH2:36]>C(OCC)(=O)C>[CH2:12]([C:14]1[CH:20]=[C:19]([OH:36])[CH:18]=[C:17]([CH2:21][CH3:22])[C:15]=1[OH:24])[CH3:13]

Participants

7

Reactant 5

HCID 962Water2×HCID 1118Sulfuric AcidHCID 113692,6-DiethylanilineHCID 24489Sodium DithioniteHCID 24502Potassium Dichromate

Product 1

HCID 142582052,6-Diethylbenzene-1,4-diol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of potassium dichromate (20 g) in water (278 mL) was added a solution (60° C.) of 2,6-diethylaniline (15.5 mL) and conc. sulfuric acid (27.8 mL) in water (580 mL). The solution was stirred for 1 hour and then extracted with ethyl acetate. After removing the solvent, the residue was dissolved in acetone (150 mL) and refluxed with water (150 mL) and conc. sulfuric acid (5 mL) for 3 hours. The acetone was removed and the mixture was extracted with ethyl acetate. Evaporation and a quick flash column (silica gel, ethyl acetate-hexane 0% to 5%) gave a residue that was dissolved in ethyl acetate and shaken with an excess of aqueous sodium hydrosulfite. Evaporation gave 3 g of 2,6-diethylbenzene-1,4-diol that was combined with acetyl chloride (13 mL, 14.18 g) in toluene (100 mL) and refluxed for 3 hours. The solvent and the excess reagent were removed under vacuum. The residue was heated up to 110° C. with boron trifluoride-acetic acid complex (14 mL) for 48 hours. Work up and chromatography (silica gel, hexane-ethyl acetate 2% to 10%) gave 4 g of 3-acetyl-2,6-diethyl-4-hydroxyphenyl acetate.

Workup

  1. extractionextracted with ethyl acetate
  2. customAfter removing the solvent
  3. dissolutionthe residue was dissolved in acetone (150 mL)
  4. temperaturerefluxed with water (150 mL) and conc. sulfuric acid (5 mL) for 3 hours
  5. customThe acetone was removed
  6. extractionthe mixture was extracted with ethyl acetate
  7. customEvaporation
  8. customa quick flash column (silica gel, ethyl acetate-hexane 0% to 5%) gave a residue that
  9. customEvaporation

Sources & evidence

ORD record
ord-5a833a93334c4e788722360d45bc8a43
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

Loading…