Hydroquinone → HCID 86740170, compound

HRID 370430Notes

Reaction equation

HRID 370430 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[C:9](Cl)(=[O:13])[CH2:10][CH2:11][CH3:12]>[OH-].[Na+].O>[C:5]([OH:13])(=[O:6])[CH2:7][CH2:8][CH3:1].[C:9]([OH:13])(=[O:2])[CH2:10][CH2:11][CH3:12].[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2]

Participants

5

Reactant 2

HCID 785HydroquinoneHCID 8855Butyryl chloride

Product 1

HCID 86740170HCID 86740170, compoundYield 151%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

Hydroquinone (55 g) was dissolved in a solution of sodium hydroxide (40 g) in water (300 ml) and to the resulting solution was added dropwise butyryl chloride (100 g), while maintaining the temperature at 3° to 6° C. The reaction was allowed to proceed at 10° to 13° C. for 4 hours. After reaction, the mixture was extracted with benzene and the benzene extract was washed with dil. sodium hydroxide solution. The solvent was removed from the extract and the residue was dissolved in ethanol (300 ml). Recrystallization was effected by addition of water (80 ml) to the solution to give hydroquinone dibutyrate (108 g). m.p. 42°-43° C.

Workup

  1. temperaturewhile maintaining the temperature at 3° to 6° C
  2. customAfter reaction
  3. extractionthe mixture was extracted with benzene
  4. extractionthe benzene extract
  5. washwas washed with dil. sodium hydroxide solution
  6. customThe solvent was removed from the
  7. extractionextract
  8. dissolutionthe residue was dissolved in ethanol (300 ml)
  9. customRecrystallization
  10. additionwas effected by addition of water (80 ml) to the solution

Sources & evidence

ORD record
ord-afb6ca1d085d49f0bc3865c4049162d6
Source dataset
uspto-grants-1985_07
Patent number
US04526779

Reaction notes

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