Hydroquinone → HCID 178516562, compound

HRID 374205Notes

Reaction equation

HRID 374205 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6](O)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:13]([OH:15])=[S:14].C1(C=CC(O)=CC=1)[OH:24].C(=O)(O)[O-].[Na+].S(=O)(=O)(O)O.[Cl-].[Na+]>C(OCC)(=O)C.C(O)=O.O.C(COC)OC>[OH:24][CH:3]1[CH2:4][C:5](=[O:1])[C:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]([OH:15])=[S:14])=[CH:2]1

Participants

10

Reactant 5

HCID 785HydroquinoneHCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 178526187HCID 178526187, compound

Product 1

HCID 178516562HCID 178516562, compound

Reagents, catalysts & solvents 4

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

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 54.4 g. of 8-(2-furyl)-8-hydroxy-2-phenylthiooctanoic acid in 815 ml. of glyme and 610 ml. of water is added successively 0.5 g. of hydroquinone, 12.0 g. of sodium bicarbonate and 122 ml. of 90% formic acid. The resulting solution is heated at reflux temperature for 24 hours, cooled to 50° C. to produce a mixture of the 3-hydroxy and 4-hydroxy isomers. This is then treated dropwise with 40 ml. of concentrated sulfuric acid during 15 minutes. The resulting solution is refluxed for 18 hours, cooled, diluted with ethyl acetate and then saturated with sodium chloride. The organic layer is separated, washed with brine, dried and concentrated. The residue is subjected to chromatography on silica gel with chloroform progressively enriched in ether, giving 13.0 g. of the product as an oil, identified by its PMRδ 4.94 (1, broad s, CHOH).

Workup

  1. temperatureThe resulting solution is heated
  2. temperatureat reflux temperature for 24 hours
  3. customto produce
  4. additionThis is then treated dropwise with 40 ml
  5. temperatureThe resulting solution is refluxed for 18 hours
  6. temperaturecooled
  7. customThe organic layer is separated
  8. washwashed with brine
  9. customdried
  10. concentrationconcentrated
  11. customgiving 13.0 g

Sources & evidence

ORD record
ord-456665d3a6a54181928a724ead3b3cd1
Source dataset
uspto-grants-1992_11
Patent number
US05166369

Reaction notes

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