Hydroquinone → Hydroquinone mono-acetate

HRID 370420Notes

Reaction equation

HRID 370420 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].C(Cl)(=[O:11])C>[OH-].[Na+].O.O1CCCC1>[C:5]([OH:11])(=[O:6])[CH3:7].[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2]

Participants

6

Reactant 2

HCID 785HydroquinoneHCID 6367Acetyl chloride

Product 1

HCID 21327627Hydroquinone mono-acetateYield 55.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

Hydroquinone (440 g) was dissolved in a solution of sodium hydroxide (160 g) in water (1600 ml) and to the resulting solution was added dropwise a solution of acetyl chloride (346 g) in tetrahydrofuran (346 g), while maintaining the temperature at 0° C. with ice-cooling. After addition, the mixture was stirred at 0° C. for 1 hour and then at room temperature for 2 hours. The reaction mixture was extracted with ethyl acetate. The ethyl acetate extract was washed with a small amount of water. Ethyl acetate was removed and the residue was distilled under a reduced pressure to give hydroquinone monoacetate (188 g). b.p. 144°-147° C./4 mmHg.

Workup

  1. temperaturecooling
  2. additionAfter addition
  3. waitat room temperature for 2 hours
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. washwas washed with a small amount of water
  7. customEthyl acetate was removed
  8. distillationthe residue was distilled under a reduced pressure

Sources & evidence

ORD record
ord-53b5e3111b44401eafaac05b4c00489c
Source dataset
uspto-grants-1985_07
Patent number
US04526779

Reaction notes

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