Benzene → Phthalimide

HRID 1973123Notes

Reaction equation

HRID 1973123 reaction equation
[C:1]1(=O)[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.C=C(CCCC#N)CCCC#[N:18].C1C=CC=CC=1>P(=O)(O)(O)O.O>[C:1]1(=[O:6])[NH:18][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12

Participants

6

Reactant 3

HCID 241BenzeneHCID 6811Phthalic AnhydrideHCID 30165315-Methylenenonanedinitrile

Product 1

HCID 6809PhthalimideYield 199.4%

Reagents, catalysts & solvents 2

HCID 1004Phosphoric AcidCatalystHCID 962WaterSolvent

Conditions

Temperature
240 °C

Procedure

225 g (1.52 moles) of phthalic anhydride, 121.5 g (0.75 mole) of 5-methylene-1,9-nonanedinitrile, 300 cc of benzene, 40 g of water and 2 g of phosphoric acid were placed in a 1-liter autoclave. The autoclave was closed, then purged with dry nitrogen. Following purging, the reactor was heated to 240° C for a period of 4 hours. After cooling, the reaction mixture was filtered. The filter solid, after being washed in 300 cc of benzene, filtered and dried, yielded 220 g of phthalimide having a melting point of 234°-238° C. Yield 100 percent.

Workup

  1. customThe autoclave was closed
  2. custompurged with dry nitrogen
  3. customFollowing purging
  4. temperatureAfter cooling
  5. filtrationthe reaction mixture was filtered
  6. washThe filter solid, after being washed in 300 cc of benzene
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-235c45dc691d4055bfddb37114316e02
Source dataset
uspto-grants-1976_12
Patent number
US03996239

Reaction notes

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