Sulfuric Acid → HCID 13548203, compound

HRID 539864Notes

Reaction equation

HRID 539864 reaction equation
C([C:4]1[CH:5]=[CH:6][C:7]([O:12][CH2:13][CH2:14][CH3:15])=[C:8]([CH:11]=1)[C:9]#[N:10])(=O)C.S(OOS([O-])(=O)=O)([O-])(=O)=[O:17].[NH4+].[NH4+].S(=O)(=O)(O)O>C(O)(=O)C>[OH:17][C:4]1[CH:5]=[CH:6][C:7]([O:12][CH2:13][CH2:14][CH3:15])=[C:8]([CH:11]=1)[C:9]#[N:10]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 62648Ammonium PersulfateHCID 86659944HCID 86659944, compound

Product 1

HCID 13548203HCID 13548203, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
45 °C

Procedure

5-acetyl-2-n-propoxybenzonitrile (20.3 g, 0.10 mol) was dissolved in glacial acetic acid (100 ml), followed by addition of ammonium persulfate (60 g, 0.26 mol). After sulphuric acid solution (H2SO4 10 ml/H2O 14 ml) was slowly added dropwise under ice-water bath, the reaction temperature was raised to 45° C. for 3 h. The reaction mixture was poured into ice water to generate precipitates, stirred for 0.5 h, filtered, and dried to give the title compound (13.0 g, yield: 73%). 1H NMR (CDCl3) δ: 8.00 (1H, d), 7.04 (1H, dd), 6.90 (1H, d), 4.05 (2H, t), 1.78 (2H, m), 1.01 (3H, t).

Workup

  1. customto generate precipitates
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-0c7ff6b38d02465fbeccb03c8464d9e1
Source dataset
uspto-grants-2014_10
Patent number
US08871777B2

Reaction notes

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