Hydrochloric Acid → HCID 67821679, compound

HRID 1655660Notes

Reaction equation

HRID 1655660 reaction equation
[C:1]1(=[O:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]([O:9][C:10](=[O:21])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH:19]=O)[CH3:8].Cl>C1C=CC=CC=1>[CH2:7]([O:9][C:10]([CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1/[CH:19]=[C:2]1/[C:1](=[O:6])[CH2:5][CH2:4][CH2:3]/1)=[O:21])[CH3:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8452CyclopentanoneHCID 345961ethyl 2-(2-formylphenoxy)acetate

Product 1

HCID 67821679HCID 67821679, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 21.2 g of morpholine enamine of cyclopentanone, 24.0 g of 2-formylphenoxyacetic acid ethyl ester, and 200 ml of benzene was refluxed through a condenser equipped with a Dean-Stark trap for about 4.5 hours. The resulting solution was cooled to about room temperature, and treated with 35 ml of 6 normal (N) hydrochloric acid. After stirring for about 2 hours at about room temperature, the benzene layer was separated and the aqueous layer was extracted with two 15 ml portions of benzene. The combined benzene layer and extracts were washed with 5% sodium bicarbonate and saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After removal of the solvent in vacuo, 27.6 g of nearly pure product was obtained. The product was crystallized in 50% ethanol to give 26.0 g of 2-(E)-(2-ethoxycarbonylmethoxyl-benzylidene) cyclopentanone as colorless crystals. The melting point of this intermediate compound was determined to be 77°-79° C.

Workup

  1. customequipped with a Dean-Stark trap for about 4.5 hours
  2. temperatureThe resulting solution was cooled to about room temperature
  3. customthe benzene layer was separated
  4. extractionthe aqueous layer was extracted with two 15 ml portions of benzene
  5. washThe combined benzene layer and extracts were washed with 5% sodium bicarbonate and saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customAfter removal of the solvent in vacuo, 27.6 g of nearly pure product
  8. customwas obtained
  9. customThe product was crystallized in 50% ethanol

Sources & evidence

ORD record
ord-d66d64a51d3b4de980069565eb9fc4a8
Source dataset
uspto-grants-1993_10
Patent number
US05250735

Reaction notes

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