Acetic Acid → HCID 10976084, compound

HRID 1758025Notes

Reaction equation

HRID 1758025 reaction equation
[CH3:1][C:2]1[C:8]([CH3:9])=[C:7]([OH:10])[CH:6]=[CH:5][C:3]=1[OH:4].[C:11](O)(=[O:13])[CH3:12]>>[CH3:1][C:2]1[C:8]([CH3:9])=[C:7]([OH:10])[CH:6]=[C:5]([C:11](=[O:13])[CH3:12])[C:3]=1[OH:4]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 691002,3-Dimethylhydroquinone

Product 1

HCID 10976084HCID 10976084, compound

Conditions

Temperature
80 °C

Procedure

276 g (2 mole) of 2,3-dimethyl-hydroquinone were suspended in 300 ml of acetic acid and heated to 80° C. with stirring. Through the obtained solution boron trifluoride was bubbled whereby care was taken that the temperature did not exceed 100° C. The reaction mixture was stirred at 120° C. for 3.5 h and then poured into 4 l of ice-water containing 500 g of dissolved sodium acetate. This mixture was stirred for 12 h till the precipitate could be separated by suction. This precipitate was then treated with 3 l of water whereto enough sodium hydrogen carbonate was added to reach a final pH of 7.5. The precipitate was suction filtered again, washed with water till neutral and recrystallized from toluene. Yield: 230 g. Melting point: 151° C. (structure confirmed by NMR).

Workup

  1. customThrough the obtained solution boron trifluoride was bubbled whereby care
  2. customdid not exceed 100° C
  3. stirringThe reaction mixture was stirred at 120° C. for 3.5 h
  4. additionpoured into 4 l of ice-water containing 500 g of dissolved sodium acetate
  5. stirringThis mixture was stirred for 12 h till the precipitate
  6. customcould be separated by suction
  7. additionThis precipitate was then treated with 3 l of water whereto enough sodium hydrogen carbonate
  8. additionwas added
  9. filtrationfiltered again
  10. washwashed with water till neutral and
  11. customrecrystallized from toluene

Sources & evidence

ORD record
ord-c965d109ad214503a5ffcda2b9deb0bd
Source dataset
uspto-grants-1983_02
Patent number
US04371604

Reaction notes

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