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

HRID 54576

Reaktionsgleichung

Reaktionsgleichung von HRID 54576
[H-].[Na+].[C:3](=[O:10])([O:7][CH2:8][CH3:9])OCC.[CH3:11][C:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)=[O:13].C(O)(=O)C.C(C1C=CC=CC=1)(=O)C>C1(C)C=CC=CC=1.O>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:12](=[O:13])[CH2:11][C:3]([O:7][CH2:8][CH3:9])=[O:10])=[CH:15][CH:16]=1

Komponenten

8

Edukt 5

HCID 176Acetic AcidHCID 7410AcetophenoneHCID 74764'-MethoxyacetophenoneHCID 7766Diethyl CarbonateHCID 24758Sodium hydride

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel6×

Versuchsvorschrift

Simultaneous reactions were run in both a 65-L reactor and a 35-L reactor that share the same reflux system. A nitrogen atmosphere was maintained in both. 4.0 kg (100 moles) of 60% sodium hydride in mineral oil and 32 L toluene were charged into the ambient temperature reactors. The mixture was agitated for 5 minutes and allowed to settle. 20 L of the toluene solution was aspirated. 28 L of toluene was added, agitated for 5 minutes, allowed to settle and 28 L of the toluene solution was aspirated. 68 L of toluene and 8.4 L (69.7 moles) diethyl carbonate were added. The agitation was begun and the flow of Syltherm (Note 4) in reactor jackets was initiated. A solution of 5.0 kg (33.3 moles) 4-methoxyacetophenone in 12 L toluene was added over 20 minutes. When additions were complete, the jacket temperaturewas reduced to 10° C. and stirring continued for 16 hours. A solution of 6.7 L (117 moles) glacial acetic acid in 23 L deionized water was fed at the same rate that was previously used for the acetophenone solution. When addition was complete, agitation was stopped and the layers separated. The aqueous layer was washed once with 13 L toluene. The combined organic layers were washed twice with 6.7 L portions of 7% (w:w) aqueous sodium bicarbonate. The toluene solution was washed once with 6.7 L of 23% (w:w) aqueous sodium chloride. The organinc solution was dried over 10 kg sodium sulfate, filtered, and the solvent removed on the rotary evaporator to provide the desired product.

Aufarbeitung

  1. temperatureA nitrogen atmosphere was maintained in both
  2. stirringagitated for 5 minutes
  3. customthe flow of Syltherm (Note 4) in reactor jackets was initiated
  4. customtemperaturewas reduced to 10° C.
  5. stirringstirring
  6. waitcontinued for 16 hours
  7. additionWhen addition
  8. customthe layers separated
  9. washThe aqueous layer was washed once with 13 L toluene
  10. washThe combined organic layers were washed twice with 6.7 L portions of 7% (w:w) aqueous sodium bicarbonate
  11. washThe toluene solution was washed once with 6.7 L of 23% (w:w) aqueous sodium chloride
  12. dry with materialThe organinc solution was dried over 10 kg sodium sulfate
  13. filtrationfiltered
  14. customthe solvent removed on the rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-b59beab724cb454b9ea5d9fb5f9aa1c2
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05622971

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