Acetone → Methyl Benzoate

HRID 27464

Reaction equation

HRID 27464 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8](CCN)=[CH:7][CH:6]=1.CC(C)=O.N1C=CC=CC=1.C(OC1C=CC(Cl)=CC=1C(Cl)=O)C>O1CCOCC1>[CH3:2][O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 180Acetone2×HCID 1049PyridineHCID 128632345-Chloro-2-ethoxybenzoyl chlorideHCID 13078671Methyl 4-(2-aminoethyl)benzoate hydrochloride

Product 1

HCID 7150Methyl Benzoate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

10.5 g of 4-(2-aminoethyl)-benzoic acid methyl ester-hydrochloride were suspended in 40 ml of dioxane and 20 ml of acetone and the suspension was combined with 8 ml of pyridine. To this suspension, a solution of 10 g of 2-ethoxy-5-chloro-benzoyl chloride in a small amount of acetone was added dropwise, while stirring, and the whole was heated for 2 hours under reflux. After cooling, the mixture was concentrated under reduced pressure, combined with ice-water, filtered with suction, stirred with dilute hydrochloric acid and with a NaHCO3 solution and the resulting product was again filtered off with suction and recrystallized from ethanol. The 4-(2-<2-ethoxy-5-chloro-benzamido>-ethyl)-benzoic acid methyl ester obtained was found to melt at 110° C.

Workup

  1. temperaturethe whole was heated for 2 hours
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. concentrationthe mixture was concentrated under reduced pressure
  5. filtrationfiltered with suction
  6. stirringstirred with dilute hydrochloric acid and with a NaHCO3 solution
  7. filtrationthe resulting product was again filtered off with suction
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-d8c8439507124513a02669ff6acf8f0e
Source dataset
uspto-grants-1980_09
Patent number
US04221815

Linked notes

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