Hydroquinone → HCID 25165906, compound

HRID 370428Notes

Reaction equation

HRID 370428 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[C:9](Cl)(=[O:11])[CH3:10]>[OH-].[Na+].O.O1CCCC1.C(Cl)(Cl)Cl>[C:5]([OH:11])(=[O:6])[CH3:7].[C:9]([OH:11])(=[O:2])[CH3:10].[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2]

Participants

7

Reactant 2

HCID 785HydroquinoneHCID 6367Acetyl chloride

Product 1

HCID 25165906HCID 25165906, compoundYield 152.2%

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

Hydroquinone (110 g) was dissolved in a solution of sodium hydroxide (80 g) in water (400 ml) and to the resulting solution was added dropwise a solution of acetyl chloride (157 g) in tetrahydrofuran (157 g) with ice-cooling (0° C.). The reaction mixture was allowed to stand overnight at room temperature. The reaction mixture was poured into water (1 liter) and the crystals formed was filered and dissolved in chloroform. The solution was washed with dil. sodium hydroxide solution to remove unreacted hydroquinone. After removal of the solvent, the residue was recrystallized from water/ethanol to give hydroquinone diacetate (175 g). m.p. 121°-122.5° C.

Workup

  1. customthe crystals formed
  2. washThe solution was washed with dil. sodium hydroxide solution
  3. customto remove unreacted hydroquinone
  4. customAfter removal of the solvent
  5. customthe residue was recrystallized from water/ethanol

Sources & evidence

ORD record
ord-e1e7a81f75314c70bc64ccf9456ac1aa
Source dataset
uspto-grants-1985_07
Patent number
US04526779

Reaction notes

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