Bisphenol A → Ether phthalimide

HRID 1680381Notes

Reaction equation

HRID 1680381 reaction equation
OC1C=CC(C(C2C=[CH:15][C:14]([OH:17])=CC=2)(C)C)=CC=1.C[O-].[Na+].[O-][C:22]1C=CC=C[CH:23]=1.[O-]C1C=CC=CC=1.[Na+].[Na+].[N+]([C:40]1[CH:41]=[C:42]2[C:47](=[O:48])[N:46](C)[C:44](=[O:45])[C:43]2=[CH:50][CH:51]=1)([O-])=O>CO.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:22][CH2:23][O:17][CH2:14][CH3:15].[C:47]1(=[O:48])[NH:46][C:44](=[O:45])[C:43]2=[CH:50][CH:51]=[CH:40][CH:41]=[C:42]12

Participants

8

Reactant 4

HCID 6623Bisphenol AHCID 923214-Nitro-N-methylphthalimideHCID 10942334Sodium MethoxideHCID 15819849Dinatriumphenolat

Product 1

HCID 18959638Ether phthalimide

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

Reaction was effected between equal molar amounts of bisphenol-A and sodium methoxide in anhydrous methanol. A mixture of 1.99 part of the resulting sodium bisphenoxide salt, 3.02 part of 4-nitro-N-methylphthalimide, 4.71 parts of tetrabutylammonium bromide which was 2 equivalents, and about 21 parts of toluene, was heated at reflux under nitrogen for 22 hours. The reaction mixture was cooled to room temperature and was extracted with a mixture of methylene chloride and 1.2 normal HCl. The resulting organic solution was dried and concentrated. The resulting mixture was stirred with methanol and filtered resulting in 2.35 parts of an ether phthalimide of the formula, ##STR7## having a melting point of 145°-147° C.

Workup

  1. customReaction
  2. temperatureat reflux under nitrogen for 22 hours
  3. extractionwas extracted with a mixture of methylene chloride and 1.2 normal HCl
  4. customThe resulting organic solution was dried
  5. concentrationconcentrated
  6. filtrationfiltered

Sources & evidence

ORD record
ord-97c3713e46554e30b4282328653fc470
Source dataset
uspto-grants-1981_06
Patent number
US04273712

Reaction notes

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