Hydroquinone → HCID 20287613, compound

HRID 126745Notes

Reaction equation

HRID 126745 reaction equation
[O:1]1C=CC=[C:2]1[C:6]([CH:8]([OH:24])[CH2:9][CH2:10]CCCC(C1C=CC=CC=1)C(O)=S)=O.[C:25]1([CH:32]=[CH:31][C:29](O)=[CH:28][CH:27]=1)O.[C:33](=[O:36])(O)[O-:34].[Na+].[S:38](=O)(=O)(O)O.[Na+].[Cl-]>C(OCC)(=O)C.C(O)=O.O.C(COC)OC>[C:33]([C:25]1[C:32]([S:38][C:10]2[C:2](=[O:1])[CH2:6][CH:8]([OH:24])[CH:9]=2)=[CH:31][CH:29]=[CH:28][CH:27]=1)([OH:34])=[O:36]

Participants

10

Reactant 5

HCID 785HydroquinoneHCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 178519700HCID 178519700, compound

Product 1

HCID 20287613HCID 20287613, compound

Reagents, catalysts & solvents 4

HCID 284Formic AcidSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred mixture of 54.4 g of 8-(2-furoyl)-8-hydroxy-2-phenylthiooctanoic acid, 0.5 g of hydroquinone, 8.5 ml of dimethoxyethane, and 6.0 ml of water is added 12.0 g of sodium bicarbonate and 122 ml of 90% formic acid. The resulting solution is stirred at reflux temperature for 24 hours. The solution is cooled, treated dropwise with 40 ml of 98% sulfuric acid during 15 min., and then refluxed for 18 hours. The solution is cooled, diluted with ethyl acetate, and saturated with solid NaCl. The organic layer is washed with brine, dried over MgSO4, and concentrated. The residue is subjected to column chromatography on silica gel with chloroform progressively enriched in ether to give an oil.

Workup

  1. temperatureat reflux temperature for 24 hours
  2. temperatureThe solution is cooled
  3. temperaturerefluxed for 18 hours
  4. temperatureThe solution is cooled
  5. washThe organic layer is washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customto give an oil

Sources & evidence

ORD record
ord-6ae150c83c3645ef89fb3706546848f3
Source dataset
uspto-grants-1981_03
Patent number
US04254036

Reaction notes

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