Ethyl benzoate → Benzoic Acid

HRID 1441143Notes

Reaction equation

HRID 1441143 reaction equation
C([O:3][C:4](=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)C.[OH-].[K+]>C(O)C>[C:4]([OH:11])(=[O:3])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 7165Ethyl benzoateHCID 14797Potassium Hydroxide

Product 1

HCID 243Benzoic Acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 4-(7-methyl-2,4-bis-pyrrolidin-1-yl-7H-pyrrolo 2,3-d!pyrimidin-6-yl)benzoic acid ethyl ester (EXAMPLE 180, 2.04 g) in ethanol (95%, 80 ml) is treated with 240 ml of a 0.1N aqueous mixture of potassium hydroxide. The mixture is heated at reflux for two days and then partially concentrated under reduced pressure. The resulting mixture is poured onto 300 ml of 5% aqueous hydrochloric acid and extracted with 5 portions of chloroform. The combined organics are dried and concentrated, the concentrate is chromatographed over silica gel, eluting with methanol/chloroform/acetic acid (5/94/1) to give the title compound, mp 290°-295°.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for two days
  3. concentrationpartially concentrated under reduced pressure
  4. additionThe resulting mixture is poured onto 300 ml of 5% aqueous hydrochloric acid
  5. extractionextracted with 5 portions of chloroform
  6. customThe combined organics are dried
  7. concentrationconcentrated
  8. customthe concentrate is chromatographed over silica gel
  9. washeluting with methanol/chloroform/acetic acid (5/94/1)

Sources & evidence

ORD record
ord-d6151d2a22f7479ca1c7a3e172d6b360
Source dataset
uspto-grants-1996_03
Patent number
US05502187

Reaction notes

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