Hydrochloric Acid → Phthalic Acid

HRID 1087996Notes

Reaction equation

HRID 1087996 reaction equation
[OH-:1].[K+].ClC1C=CC=CC=1C[C:7]1[CH:17]=[CH:16][CH:15]=[C:9]2[C:10](N[C:13](=[O:14])[C:8]=12)=[O:11].Cl.[OH2:23]>>[C:10]([OH:11])(=[O:23])[C:9]1[C:8](=[CH:7][CH:17]=[CH:16][CH:15]=1)[C:13]([OH:14])=[O:1]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 14797Potassium HydroxideHCID 22164415HCID 22164415, compound

Product 1

HCID 1017Phthalic AcidYield 98%

Conditions

Temperature
126.5 °C

Procedure

A 2 L, round-bottomed, 3-necked flask was charged with 830 g of 50% aqueous potassium hydroxide solution, and 333 g of 2-chlorobenzylphthalimide. The reaction mixture was then heated under reflux (pot temperature 125-128° C.) for 21 hours with stirring. It was then cooled in iced-water and allowed to settle in a separating funnel. The lower aqueous layer was drained, diluted with 2 L of water and acidified with 676 g of concentrated hydrochloric acid (with cooling). This caused the formation of a white precipitate, which was collected by filtration and dried in a vacuum oven overnight to yield 199.9 g of phthalic acid (98%). The organic layer was essentially pure (99.9% by GC) 2-chlorobenzylamine (163.4 g, 1.15 mol, 93.5%).

Workup

  1. temperatureThe reaction mixture was then heated
  2. customto settle in a separating funnel
  3. filtrationwas collected by filtration
  4. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-95af77dda314427db2c7f11c689e27b9
Source dataset
uspto-grants-1990_10
Patent number
US04960938

Reaction notes

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