Hydrochloric Acid → HCID 86605484, compound

HRID 2103034Notes

Reaction equation

HRID 2103034 reaction equation
C([O:4][C:5]1[CH:10]=[C:9]([C:11](=O)[CH3:12])[C:8]([OH:14])=[C:7]([CH3:15])[C:6]=1[CH3:16])(=O)C.O.Cl>C1(C)C=CC=CC=1.[Zn].Cl[Hg]Cl>[CH2:11]([C:9]1[C:8]([OH:14])=[C:7]([CH3:15])[C:6]([CH3:16])=[C:5]([OH:4])[CH:10]=1)[CH3:12]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 9794488HCID 9794488, compound

Product 1

HCID 86605484HCID 86605484, compoundYield 99.6%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24085Mercuric ChlorideCatalystHCID 1140TolueneSolvent

Procedure

To a well stirred solution of 5-acetyl-4-hydroxy-2,3-dimethylphenyl acetate (4.7 g) in 100 mL of toluene were added Zn dust (5.0 g), HgCl2 (480 mg), water (9 mL) and concentrated HCl (9 mL). The heterogeneous mixture was allowed to reflux for 2 days. The mixture was cooled, filtered, and extracted with ethyl acetate. The organic layer was washed with saturated NaHCO3 and water, and dried over anhydrous Na2SO4. Evaporation of the organic solvents gave 3.5 g of 5-ethyl-2,3-dimethylbenzene-1,4-diol as an off-white powder.

Workup

  1. temperatureto reflux for 2 days
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated NaHCO3 and water
  6. dry with materialdried over anhydrous Na2SO4
  7. customEvaporation of the organic solvents

Sources & evidence

ORD record
ord-d0f0f4f803df454d94cd237a19c3c343
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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