Hydroquinone → HCID 70478473, compound

HRID 370431Notes

Reaction equation

HRID 370431 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[C:9](Cl)(=[O:14])[CH2:10][CH2:11][CH2:12][CH3:13]>[OH-].[Na+].O>[C:5]([OH:6])(=[O:14])[CH2:7][CH2:8][CH2:1][CH3:3].[C:9]([OH:14])(=[O:2])[CH2:10][CH2:11][CH2:12][CH3:13].[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2]

Participants

5

Reactant 2

HCID 785HydroquinoneHCID 61186Valeryl chloride

Product 1

HCID 70478473HCID 70478473, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

Hydroquinone (45.6 g) was dissolved in a solution of sodium hydroxide (33.2 g) in water (332 ml) and to the resulting solution was added dropwise valeryl chloride (100 g), while maintaining the temperature at 3° to 6° C. The reaction was allowed to proceed at 15° C. for 1 hour. After reaction, the mixture was extracted with benzene and the benzene extract was washed with dil. sodium hydroxide solution to remove unreacted hydroquinone. The solvent was removed from the extract and the residue was distilled under a reduced pressure to give crude crystals (40 g) which were recrystallized from ethanol to give hydroquinone divalerate (36 g). b.p. 155°-157° C./1 mmHg.

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. customto remove unreacted hydroquinone
  7. customThe solvent was removed from the
  8. extractionextract
  9. distillationthe residue was distilled under a reduced pressure
  10. customto give crude crystals (40 g) which
  11. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-717a316e272b46d191bff45c3e93260f
Source dataset
uspto-grants-1985_07
Patent number
US04526779

Reaction notes

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