Phenyl phosphorus dichloride → 3-Chlorophthalic anhydride

HRID 2231961Notes

Reaction equation

HRID 2231961 reaction equation
ClCl.[Cl:3]P(Cl)C1C=CC=CC=1.[N+]([C:15]1[CH:25]=[CH:24][CH:23]=[C:17]2[C:18]([O:20][C:21](=[O:22])[C:16]=12)=[O:19])([O-])=O.[OH-].[Na+]>ClP(=O)(Cl)C1C=CC=CC=1>[Cl:3][C:15]1[CH:25]=[CH:24][CH:23]=[C:17]2[C:18]([O:20][C:21](=[O:22])[C:16]=12)=[O:19]

Participants

6

Reactant 4

HCID 12573Phenyl phosphorus dichlorideHCID 14798Sodium HydroxideHCID 216313-Nitrophthalic anhydrideHCID 24526Chlorine

Product 1

HCID 670143-Chlorophthalic anhydrideYield 82.5%

Reagents, catalysts & solvents 1

HCID 69990Phenylphosphonic dichlorideSolvent

Conditions

Temperature
150 °C

Procedure

Chlorine gas (363 milligrams, 5.18 millimoles) was bubbled into a solution of dichlorophenylphosphine (927 milligrams, 5.18 millimoles) in dichlorophenylphosphine oxide (10 milliliters). To this yellow solution was added 3-nitrophthalic anhydride (1 gram, 5.18 millimoles), then the reaction mixture was heated to 150° C. for 12 hours. The cooled solution was poured onto ice (20 milliliters) and neutralized with 50% aqueous sodium hydroxide. The aqueous mixture was extracted twice with 20 milliliter portions of ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulfate and concentrated in vacuo to yield 3-chlorophthalic anhydride (780 milligrams, 83 weight percent) as a dark solid.

Workup

  1. additionThe cooled solution was poured onto ice (20 milliliters)
  2. extractionThe aqueous mixture was extracted twice with 20 milliliter portions of ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5dee690a76b842979bfb92ddcea7b742
Source dataset
uspto-grants-1988_11
Patent number
US04785121

Reaction notes

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