Phthalic Anhydride → 2-(4-Tert-butyl-3-hydroxyphenyl)isoindoline-1,3-dione

HRID 383386Notes

Reaction equation

HRID 383386 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]([CH3:12])([CH3:11])[CH3:10])=[C:6]([OH:8])[CH:7]=1.[C:13]1(=O)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[O:14]1.C(N(CC)CC)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:9]([C:5]1[CH:4]=[CH:3][C:2]([N:1]2[C:13](=[O:14])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:22])=[CH:7][C:6]=1[OH:8])([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 6811Phthalic AnhydrideHCID 8471TriethylamineHCID 574702095-Amino-2-(tert-butyl)phenol

Product 1

HCID 593950032-(4-Tert-butyl-3-hydroxyphenyl)isoindoline-1,3-dioneYield 84%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5-amino-2-tert-butyl-phenol (300 mg, 1.82 mmol), isobenzofuran-1,3-dione (283 mg, 1.91 mmol), triethylamine (759 μL, 5.45 mmol) in toluene (5.0 mL) was stirred at 110° C. for 13 h. The reaction mixture was cooled, diluted with ethyl acetate (15 mL), and washed with 10% aqueous NaHCO3(10 mL) and water. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to provide 2-(4-tert-butyl-3-hydroxyphenyl)isoindoline-1,3-dione (450 mg, 84% yield) as a light brown solid which was used for next reaction without further purification. 1H NMR (400.0 MHz, DMSO-d6) δ 9.72 (s, 1H), 7.96 (m, 2H), 7.90 (m, 2H), 7.25 (d, J=8.3 Hz, 1H), 6.85 (d, J=2.0 Hz, 1H), 6.79 (dd, J=2.1, 8.3 Hz, 1H), 1.38 (s, 9H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with 10% aqueous NaHCO3(10 mL) and water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f1abcb6dd538481d82e913ae6c106cd1
Source dataset
uspto-grants-2013_02
Patent number
US08367660B2

Reaction notes

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