Acetic Acid → HCID 14618000, compound

HRID 1692531Notes

Reaction equation

HRID 1692531 reaction equation
[C:1]1([C:7]2[CH:23]=[CH:22][C:10]([O:11][C:12]3[CH:13]=[C:14](C#N)[C:15](=[CH:18][CH:19]=3)C#N)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)[OH:25].[C:29]([OH:32])(=[O:31])[CH3:30]>>[C:1]1([C:7]2[CH:23]=[CH:22][C:10]([O:11][C:12]3[CH:13]=[C:14]4[C:15](=[O:25])[O:32][C:29](=[O:31])[C:30]4=[CH:18][CH:19]=3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 746627HCID 746627, compound

Product 1

HCID 14618000HCID 14618000, compoundYield 99%

Conditions

Temperature
120 °C

Procedure

A 1 L 3-necked round-bottomed flask was equipped with a condenser, mechanical stirrer, and an addition funnel. The flask was charged with 4-(4-phenylphenoxy)-phthalonitrile (71 g, 0.24 mole) and acetic acid (450 mL). The addition funnel was filled with 70% sulfuric acid (200 mL). The solution was heated to 120° C., and then sulfuric was added drop-wise into the reaction mixture over 2 hours. The resulting mixture was refluxed overnight (12 hours). The reaction mixture was cooled to room temperature, and poured into an ice-water mixture (˜1 kg). The product precipitated out as a pale brown powder. The powder was collected by filtration, and it was further purified by recrystallization using acetic anhydride (255 mL). The crystal was collected by filtration and dried in a vacuum oven at 150° C. overnight to give the desired product (75.0 g, 99% yield). MP 199° C. 1H NMR (δ, D6-DMSO): 8.11 (d, 1H), 7.82 (d, 2H), 7.71 (d, 2H), 7.58 (dd, 1H), 7.55-7.35 (m, 4H), 7.30 (d, 2H).

Workup

  1. customA 1 L 3-necked round-bottomed flask was equipped with a condenser, mechanical stirrer, and an addition funnel
  2. additionsulfuric was added drop-wise into the reaction mixture over 2 hours
  3. temperatureThe resulting mixture was refluxed overnight (12 hours)
  4. temperatureThe reaction mixture was cooled to room temperature
  5. customThe product precipitated out as a pale brown powder
  6. filtrationThe powder was collected by filtration, and it
  7. customwas further purified by recrystallization
  8. filtrationThe crystal was collected by filtration
  9. customdried in a vacuum oven at 150° C. overnight

Sources & evidence

ORD record
ord-9f6e32992b4546de82f6d31c0b89bfa4
Source dataset
uspto-grants-2012_04
Patent number
US08158243B2

Reaction notes

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