Hydroquinone → 2,5-Bis(3,7-dimethyloctan-3-yl)benzene-1,4-diol

HRID 1390178Notes

Reaction equation

HRID 1390178 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[CH3:9][C:10](O)([CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:11][CH3:12].S(=O)(=O)(O)O>CO>[CH2:11]([C:10]([C:3]1[CH:4]=[C:5]([OH:6])[C:7]([C:10]([CH3:9])([CH2:11][CH3:12])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:8][C:1]=1[OH:2])([CH3:9])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH3:12]

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 1118Sulfuric AcidHCID 6548Tetrahydrolinalool

Product 1

HCID 148177402,5-Bis(3,7-dimethyloctan-3-yl)benzene-1,4-diolYield 33.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

55 g of hydroquinone and 71.5 g of 3,7-dimethyloctan-3-ol were dissolved in 100 ml of methanol. Then, 50 ml of concentrated sulfuric acid (36 N) was added dropwise thereto under stirring and cooling so as to maintain the temperature at 40° C. or less. Subsequently, the reaction mixture was maintained at 50° to 55° C. for 4 hours. The resulting reaction mixture was added to ice-water, and extracted with 500 ml benzene. The benzene layer was washed with water and, after drying over anhydrous sodium sulfate, benzene and unreacted 3,7-dimethyloctan-3-ol were distilled off under reduced pressure. The residual oil was chromatographed on silica gel using benzene as a developing solvent. Thus, 29.8 g of 2,5-bis(1-ethyl-1,5-dimethylhexyl)hydroquinone (the same compound as obtained in Synthesis Example 1) was first eluted, and then 15.1 g of 2-(1-ethyl-1,5-dimethylhexyl)hydroquinone was eluted.

Workup

  1. temperaturecooling so as
  2. temperatureto maintain the temperature at 40° C. or less
  3. temperatureSubsequently, the reaction mixture was maintained at 50° to 55° C. for 4 hours
  4. customThe resulting reaction mixture
  5. extractionextracted with 500 ml benzene
  6. washThe benzene layer was washed with water
  7. dry with materialafter drying over anhydrous sodium sulfate, benzene and unreacted 3,7-dimethyloctan-3-ol
  8. distillationwere distilled off under reduced pressure
  9. customThe residual oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-eb0cb0453d834f7aa1cc68b310c25b9d
Source dataset
uspto-grants-1979_02
Patent number
US04138259

Reaction notes

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