Azobisisobutyronitrile → HCID 20728721, compound

HRID 1583110Notes

Reaction equation

HRID 1583110 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:17][CH:16]=2)[C:4]=1[C:5]([O:7][CH3:8])=[O:6])=[CH2:2].[C:25]([OH:28])(=[S:27])[CH3:26].CC(N=NC(C#N)(C)C)(C#N)C>C1C=CC=CC=1>[C:25]([S:27][CH2:2][CH2:1][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:20]=2)[C:4]=1[C:5]([O:7][CH3:8])=[O:6])(=[O:28])[CH3:26]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 20728726HCID 20728726, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 20728721HCID 20728721, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 2-ethenyl-6-[4-(methoxycarbonyl)phenyl]methoxy-benzoic acid, methyl ester (0.71 g, 2.18 mmol) in benzene (10 mL) was added thioacetic acid (1.80 mL, 25.2 mmol) followed by AIBN (37 mg, 0.23 mmol). After nitrogen was bubbled through the solution for 30 min, the solution was heated at reflux for 4 h. The reaction was allowed to cool to rt and saturated NaHCO3 (20 mL) was added. The mixture was extracted with EtOAc (3×20 mL). The combined organic extracts were washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (1:10 EtOAc/hexanes) to give 2-[2-(acetylthio)ethyl]-6-[4-(methoxycarbonyl)phenyl]methoxy-benzoic acid, methyl ester (0.50 g, 60%) as a clear oil: 1H NMR (CDCl3) δ2.34 (s, 3H), 2.85-2.82 (m, 2H), 3.07-3.10 (m, 2H), 3.92 (s, 3H), 3.94 (s, 3H), 5.16 (s, 2H), 6.81 (d, J=8.2 Hz, 1H), 6.92 (d, J=7.7 Hz, 1H), 7.28 (t, J=8.2 Hz, 1H), 7.46 (d, J=8.3 Hz, 2H), 8.04 (d, J=8.3 Hz, 2H).

Workup

  1. customAfter nitrogen was bubbled through the solution for 30 min
  2. temperaturethe solution was heated
  3. temperatureat reflux for 4 h
  4. additionsaturated NaHCO3 (20 mL) was added
  5. extractionThe mixture was extracted with EtOAc (3×20 mL)
  6. washThe combined organic extracts were washed with water and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash chromatography (1:10 EtOAc/hexanes)

Sources & evidence

ORD record
ord-f40ad87eeb134859a727048ec198bd62
Source dataset
uspto-grants-2004_05
Patent number
US06740777B2

Reaction notes

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