Sodium Hydroxide → 3-Chlorophthalic anhydride

HRID 1194512Notes

Reaction equation

HRID 1194512 reaction equation
C1([P+](Cl)(Cl)[Cl:8])C=CC=CC=1.[N+]([C:14]1[CH:24]=[CH:23][CH:22]=[C:16]2[C:17]([O:19][C:20](=[O:21])[C:15]=12)=[O:18])([O-])=O.[OH-].[Na+]>C1(P(Cl)(Cl)=O)C=CC=CC=1>[Cl:8][C:14]1[CH:24]=[CH:23][CH:22]=[C:16]2[C:17]([O:19][C:20](=[O:21])[C:15]=12)=[O:18]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 216313-Nitrophthalic anhydrideHCID 12468898HCID 12468898, compound

Product 1

HCID 670143-Chlorophthalic anhydride

Reagents, catalysts & solvents 1

HCID 69990Phenylphosphonic dichlorideSolvent

Conditions

Temperature
170 °C

Procedure

Phenyltrichlorophosphonium hexachlorophosphide (4 g, 8.8 mM) was added to phenylphosphonic dichloride (10 ml). To this solutoin, 3 nitrophthalic anhydride (1.7 g, 8.8 mM) was added. The reaction mixture was heated to 170° C. for 12 hours, then cooled to room temperature and poured onto ice. After neutralizing with 50% aqueous sodium hydroxide, the reaction was extracted with ethyl acetate. The combined ethyl acetate extracts were washed with brine, dried over magnesium sulfate, and concentrated in vacuo to give 3-chlorophthalic anhydride (1.3 g, 81 wt. % yield) as a tan solid.

Workup

  1. temperaturecooled to room temperature
  2. additionpoured onto ice
  3. extractionthe reaction was extracted with ethyl acetate
  4. washThe combined ethyl acetate extracts were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6f1afa0d9c8a4c72bb8eaf8c89314090
Source dataset
uspto-grants-1989_03
Patent number
US04814467

Reaction notes

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