Hydroquinone → HCID 20380646, compound

HRID 1447959Notes

Reaction equation

HRID 1447959 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]([CH3:23])[CH2:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:11][CH3:12].S(=O)(=O)(O)O>COCCO>[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]([CH3:23])[CH2:17][CH2:18][CH2:19][CH:20]([CH3:21])[CH3:22])=[CH:8][C:1]=1[OH:2])([CH3:9])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:23])[CH2:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH3:12]

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 1118Sulfuric AcidHCID 237013-Dodecanol, 3,7,11-trimethyl-

Product 1

HCID 20380646HCID 20380646, compound

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

55 g of hydroquinone and 120 ml of 3,7,11-trimethyldodecan-3-ol were dissolved in 120 ml of methyl Cellosolve. 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 of benzene. The benzene layer was washed with water and, after drying over anhydrous sodium sulfate, benzene and unreacted 3,7,11-trimethyldodecan-3-ol were distilled off under reduced pressure. The residual oil was chromatographed on silica gel using benzene as a developing solvent. Thus, 41 g of 2,5-bis(1-ethyl-1,5,9-trimethyldecyl)hydroquinone (the same compound as obtained in Synthesis Example 1) was first eluted, and then 20 g of 2-(1-ethyl-1,5,9-trimethyldecyl)hydroquinone was eluted. The results of elemental analysis of the above-described monoalkyl hydroquinone are shown below.

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 of benzene
  6. washThe benzene layer was washed with water
  7. dry with materialafter drying over anhydrous sodium sulfate, benzene and unreacted 3,7,11-trimethyldodecan-3-ol
  8. distillationwere distilled off under reduced pressure
  9. customThe residual oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-4bf113866403432a8446412d07edd158
Source dataset
uspto-grants-1979_12
Patent number
US04179293

Reaction notes

Loading…