Sulfuric Acid → HCID 86720840, compound

HRID 1482173Notes

Reaction equation

HRID 1482173 reaction equation
S(=O)(=O)(O)O.COC(C1C=CC2C(=CC=CC=2)C=1C1C2C(C(C3C4C(=CC=CC=4)C=CC=3C(OC)=O)=C3C=1C=CC=C3)=CC=CC=2)=O.C(Cl)(Cl)Cl.[CH:52]1[C:57]2=[C:58]3[C:75](=[CH:76][CH:77]=[C:56]2[CH:55]=[CH:54][CH:53]=1)[C:74](=[O:78])[C:73]1[C:60]2[C:61]4[C:70](=[CH:71][CH:72]=1)[C:69](=[O:79])[C:68]1[C:63](=[C:64]5[CH:83]=[CH:82][CH:81]=[CH:80][C:65]5=[CH:66][CH:67]=1)[C:62]=4[C:84]1[CH:85]=[CH:86][CH:87]=[CH:88][C:89]=1[C:59]3=2>O>[CH:76]1[C:75]2[C:74](=[O:78])[C:73]3[C:60]4[C:59]([C:58]=2[C:57]2[C:56](=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH:77]=1)=[C:89]1[C:84]2[C:85](=[CH:86][CH:87]=[CH:88]1)[C:69](=[O:79])[C:68]1[CH:67]=[CH:66][C:65]5[C:64]([C:63]=1[C:62]=2[C:61]=4[CH:70]=[CH:71][CH:72]=3)=[CH:83][CH:82]=[CH:81][CH:80]=5

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6212ChloroformHCID 86720843HCID 86720843, compoundHCID 131736684HCID 131736684, compound

Product 1

HCID 86720840HCID 86720840, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Anthracene-9,10-diboronic acid (15.0 g, 56.4 mmol), palladium acetate (633 mg, 2.82 mmol), tri(t-butyl)phosphine (1.71 g, 8.46 mmol), methyl-1-bromonaphthalene-2-carboxylate (31.4 g, 118 mmol) and cesium carbonate (73.5 g, 226 mmol) were dissolved in 200 mL of xylene and the solution was reacted under reflux at the boiling point for 5 hours in a nitrogen atmosphere to obtain dimethyl-1,1′-(anthracene-9,10-diyl)bis(2-naphthoate) at a yield of 78%. Concentrated sulfuric acid (400 mL) was added to the dimethyl-1,1′-(anthracene-9,10-diyl)bis(2-naphthoate) (24.0 g, 44.0 mmol) to react at 180° C. for 4 hours. Thereafter, chloroform and water were added to the reaction mixture to separate the organic phase. The organic phase was washed with water and a saturated sodium chloride solution, and concentrated under reduced pressure. The resulting reaction mixture was purified by silica gel column chromatography (chloroform) to obtain dinaphtho[1,2-a:1′,2′-j]perylene-10,20-dione (yield: 28%) and dibenzo[a,o]naphtho[1,2,3,4-rst]pentaphene-7,10-dione (22%).

Workup

  1. customto react at 180° C. for 4 hours
  2. customto separate the organic phase
  3. washThe organic phase was washed with water
  4. concentrationa saturated sodium chloride solution, and concentrated under reduced pressure
  5. customThe resulting reaction mixture
  6. customwas purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-18582a70e74b48f3a28438861fe41092
Source dataset
uspto-grants-2016_08
Patent number
US09412952B2

Reaction notes

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