Fuming sulfuric acid → 1-Pentylanthracene-9,10-dione

HRID 258941Notes

Reaction equation

HRID 258941 reaction equation
OS(O)(=O)=O.O=S(=O)=O.C([C:15]1[C:16]([C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18](O)=[O:19])CCCC>ClC1C(Cl)=C(Cl)C=CC=1.O>[CH2:22]([C:15]1[C:16]2[C:24](=[O:31])[C:25]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:18](=[O:19])[C:17]=2[CH:21]=[CH:22][CH:23]=1)[CH2:23][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 2

HCID 24681Fuming sulfuric acid2×HCID 54487287HCID 54487287, compound2×

Product 1

HCID 142749431-Pentylanthracene-9,10-dioneYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 68951,2,3-TrichlorobenzeneSolvent2×

Conditions

Temperature
90 °C

Procedure

The strength of the oleum employed was 8.8%, and the concentration of amylbenzoylbenzoic acid in trichlorobenzene solution was 20%. To 447 grams of the oleum mixture there was added 406 grams of 20 % solution of amylbenzoylbenzoic acid in trichlorobenzene. The addition was made gradually over a 10 minute period while holding the temperature in the reaction mass below 20° C. The temperature was raised to 90° C and held at that level for 4 hours. Then, the reaction mixture was drowned in 2000 ml of cold water. The temperature was next adjusted to just below 70° C and the organic layer was separated by decantation. It was washed twice with 800 ml portions of water, then with 800 ml of water containing 5 grams of 30% sodium hydroxide and finally with another 800 ml of water. The washed trichlorobenzene-amylanthraquinone solution weighed 345 g. Vacuum distillation at 3 mm absolute pressure indicated 18.5% organic solids that were analyzed by vapor phase chromatography and found to be 94.2% amylanthraquinone. The yield of 100% of amylanthraquinone was 92.8% of theory.

Workup

  1. additionThe addition
  2. customin the reaction mass below 20° C
  3. waitheld at that level for 4 hours
  4. customwas next adjusted to just below 70° C
  5. customthe organic layer was separated by decantation
  6. washIt was washed twice with 800 ml portions of water
  7. distillationVacuum distillation at 3 mm absolute pressure

Sources & evidence

ORD record
ord-8b339d010e084c159edb4c73e789d9e1
Source dataset
uspto-grants-1977_07
Patent number
US04035396

Reaction notes

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