Sulfuric Acid → 2-Neopentylanthraquinone

HRID 1030835Notes

Reaction equation

HRID 1030835 reaction equation
[CH2:1]([C:6]1[CH:22]=[CH:21][C:9]([C:10]([C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]([OH:16])=O)=[O:11])=[CH:8][CH:7]=1)[C:2]([CH3:5])([CH3:4])[CH3:3].S(=O)(=O)(O)O>O>[CH2:1]([C:6]1[CH:22]=[CH:21][C:9]2[C:10](=[O:11])[C:12]3[C:13](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:14](=[O:16])[C:8]=2[CH:7]=1)[C:2]([CH3:3])([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 140079172-(4-Neopentylbenzoyl)-benzoic acid

Product 1

HCID 144530162-NeopentylanthraquinoneYield 90.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

90 g (0.3 mole) of this 2-(4-neopentylbenzoyl)-benzoic acid were introduced into 900 g of 100 percent strength sulfuric acid at 60° C. and then stirred for 4 hours at 85° C. The reaction mixture was then poured into a mixture of 1,500 g of water and 500 g of ice, and the stirred mixture was cooled. The precipitated crystals of neopentylanthraquinone were filtered off, washed neutral with dilute sodium hydroxide solution and water, dried, and distilled at 240° C./0.5 mbar. 75.3 g (89%) of 2-neopentylanthraquinone (mp. 93.8° C.) were obtained.

Workup

  1. temperaturethe stirred mixture was cooled
  2. filtrationThe precipitated crystals of neopentylanthraquinone were filtered off
  3. washwashed neutral with dilute sodium hydroxide solution and water
  4. customdried
  5. distillationdistilled at 240° C./0.5 mbar

Sources & evidence

ORD record
ord-597642b872e24db4a50ab5fa85f1da3e
Source dataset
uspto-grants-1992_04
Patent number
US05107004

Reaction notes

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