Hydroquinone → HCID 70477804, compound

HRID 370424Notes

Reaction equation

HRID 370424 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[C:9](Cl)(=[O:25])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].S(=O)(=O)(O)O>[OH-].[Na+].O1CCCC1>[C:9]([OH:25])(=[O:2])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2]

Participants

6

Reactant 3

HCID 785HydroquinoneHCID 1118Sulfuric AcidHCID 8206Palmitoyl chloride

Product 1

HCID 70477804HCID 70477804, compoundYield 54.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

Hydroquinone (55 g) was dissolved in 10% sodium hydroxide solution (200 g) and to the resulting solution was added tetrahydrofuran (50 g). A solution of palmitoyl chloride (13.7 g) in tetrahydrofuran was added dropwise to the mixture over about 1 hour, while maintaining the temperature at 0° to 5° C. The reaction mixture was stirred at the same temperature for 1 hour and then at room temperature for 2 hours. The reaction mixture was poured into dil. sulfuric acid and extracted with ethyl acetate. The ethyl acetate extract was washed with water and concentrated under a reduced pressure. The concentrate was purified by silica gel column chromatography to give hydroquinone monopalmitate (10 g). m.p. 90.5°-91.5° C.

Workup

  1. temperaturewhile maintaining the temperature at 0° to 5° C
  2. waitat room temperature for 2 hours
  3. extractionextracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed with water
  6. concentrationconcentrated under a reduced pressure
  7. customThe concentrate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9f7e1c4b8f444a00b00a863015dca916
Source dataset
uspto-grants-1985_07
Patent number
US04526779

Reaction notes

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