Benzoate → Benzoic Acid

HRID 1154342Notes

Reaction equation

HRID 1154342 reaction equation
[C:1]([O-:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>O.C(O)C>[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 242BenzoateHCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 2.1 g. of ethyl 4-(5H-dibenzo[a,d]cycloheptene-Δ5,α -acetamido) benzoate, 300 mg. of sodium hydroxide, 8 ml. of water, and 250 ml. of ethanol is refluxed for 4 hours, cooled, diluted with 500 ml. of water, and acidified with concentrated hydrochloric acid. After cooling and stirring for 30 minutes, the solid is collected, washed with water, dried, dissolved in 50 ml. of acetone, and filtered. To the filtrate is added 75 ml. of acetonitrile. The solvent is partially evaporated, and the solid is collected by filtration to yield 1.5 g. of the desired product as a white solid, m.p. 248°-250° C.

Workup

  1. additionA mixture of 2.1 g
  2. temperaturecooled
  3. additiondiluted with 500 ml
  4. temperatureAfter cooling
  5. customthe solid is collected
  6. washwashed with water
  7. customdried
  8. dissolutiondissolved in 50 ml
  9. filtrationof acetone, and filtered
  10. additionTo the filtrate is added 75 ml
  11. customThe solvent is partially evaporated
  12. filtrationthe solid is collected by filtration
  13. customto yield 1.5 g

Sources & evidence

ORD record
ord-9ab79bd56a82423ca83be1871b5cb5c6
Source dataset
uspto-grants-1984_12
Patent number
US04489090

Reaction notes

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