4-t-Butyl-2-(4-t-butylbenzoyl)benzoic acid → 2,7-Di-t-butylanthraquinone

HRID 900390

Reaction equation

[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[C:7]([C:14](=[O:25])C2C=CC(C(C)(C)C)=CC=2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>C(Cl)(Cl)Cl>[C:1]([C:5]1[CH:13]=[CH:12][C:8]2[C:9](=[O:11])[C:8]3[C:7](=[CH:6][C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])=[CH:13][CH:12]=3)[C:14](=[O:25])[C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 150 °C

Procedure

Into a 500 ml flask having the egg plant shape equipped with a condenser, 200 ml of polyphosphoric acid was placed and heated at 150° C. Then, 32 g (95 mmole) of 4-t-butyl-2-(4-t-butylbenzoyl)benzoic acid was added in small portions, and the resultant mixture was stirred at the same temperature for 3 hours. After the reaction was completed, the reaction mixture was poured into ice water, and the resultant mixture was treated by liquid-liquid extraction with chloroform. After being dried with magnesium sulfate, the extract was concentrated under a reduced pressure by a rotary evaporator. The obtained crude crystals were recrystallized from hexane, and 21 g of the anthraquinone compound of the object compound was obtained (the yield: 69%; yellow crystals).

Workup

customInto a 500 ml flask having
customthe egg plant shape equipped with a condenser
dry with materialAfter being dried with magnesium sulfate
concentrationthe extract was concentrated under a reduced pressure by a rotary evaporator
customThe obtained crude crystals
customwere recrystallized from hexane, and 21 g of the anthraquinone compound of the object compound
customwas obtained (the yield: 69%

Sources & evidence

ORD record: ord-7a09d4afdd9146cdae94a331d3449c85
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07357991B2

Linked notes

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