Hydrochloric Acid → Benzenepropanoic acid, 4-methoxy-beta-oxo-, ethyl ester

HRID 1742815Notes

Reaction equation

HRID 1742815 reaction equation
[H-].[Na+].[C:3](=[O:10])([O:7][CH2:8][CH3:9])OCC.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:21])[CH3:20])=[CH:15][CH:14]=1.Cl>O1CCCC1.O>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([CH2:20][C:3]([O:7][CH2:8][CH3:9])=[O:10])=[O:21])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 74764'-MethoxyacetophenoneHCID 7766Diethyl CarbonateHCID 24758Sodium hydride

Product 1

HCID 76150Benzenepropanoic acid, 4-methoxy-beta-oxo-, ethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In 60 ml of tetrahydrofuran was suspended 18.7 g of 60% sodium hydride followed by addition of 39.4 of diethyl carbonate. Then, a solution of 25 g of p-methoxyacetophenone in 70 ml of THF was added dropwise with refluxing and the mixture was further refluxed for 5 hours. After cooling, the reaction mixture was poured slowly into iced water, neutralized with concentrated hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated. The resulting oil was distilled under reduced pressure to provide 30.1 g of the desired compound as a pale yellow oil. b.p. 161°-164° C. (3 mmHg).

Workup

  1. temperaturewith refluxing
  2. temperaturethe mixture was further refluxed for 5 hours
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. distillationThe resulting oil was distilled under reduced pressure

Sources & evidence

ORD record
ord-c2836e9699334b0c9ec829f245e62dc1
Source dataset
uspto-grants-1994_08
Patent number
US05342845

Reaction notes

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