Dimethyl Carbonate → Methyl 4-(4-Benzyloxyphenoxy)-3-oxopentanoate

HRID 986484Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 986484
[CH2:1]([O:8][C:9]1[CH:20]=[CH:19][C:12]([O:13][CH:14]([CH3:18])[C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].[C:22](=O)([O:25]C)[O:23][CH3:24]>>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH:14]([CH3:18])[C:15](=[O:17])[CH2:16][C:22]([O:23][CH3:24])=[O:25])=[CH:19][CH:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 3

HCID 12021Dimethyl CarbonateHCID 5360545SodiumHCID 140932993-[4-(Benzyloxy)phenoxy]butan-2-one

Produkt 1

HCID 14093300Methyl 4-(4-Benzyloxyphenoxy)-3-oxopentanoate

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

3-(4-Benzyloxyphenoxy)-2-butanone (5.0 g) was dissolved in 25 ml of dimethyl carbonate and added to a 50 ml, three-necked, round-bottom flask fitted with a thermometer, condenser, magnetic stirrer and nitrogen sweep. The solution was heated to 85° C. in an oil bath, then charged with 0.51 g of sodium over a period of 0.5 hour. The resulting clear yellow solution began off-passing after 15 minutes, and then turned a cloudy yellow. After 1 hour, the condenser was replaced with a Vigreux column and distillation head, and the bath temperature was raised to 130° C. Methanol was distilled off for 45 minutes. After approximately 4.5 hours, the reaction was stopped and the solution let cool to room temperature. The dimethyl carbonate was stripped off, and the residue rediluted with 50 ml of ethyl acetate. The solution was then washed with a solution of 50 ml of ice water and 5 ml of acetic acid and then with 50 ml of water. The organic phase was dried over magnesium sulfate, filtered, and stripped. The crude yield was 6.06 g of an orange oil. This was submitted for analysis and found to contain 82% of the desired product, methyl 4-(4-benzyloxyphenoxy)-3-oxopentanoate.

Aufarbeitung

  1. additionadded to a 50 ml
  2. customthree-necked, round-bottom flask fitted with a thermometer, condenser, magnetic stirrer and nitrogen sweep
  3. waitAfter 1 hour
  4. distillationthe condenser was replaced with a Vigreux column and distillation head
  5. temperaturethe bath temperature was raised to 130° C
  6. distillationMethanol was distilled off for 45 minutes
  7. waitAfter approximately 4.5 hours
  8. temperaturethe solution let cool to room temperature
  9. additionthe residue rediluted with 50 ml of ethyl acetate
  10. washThe solution was then washed with a solution of 50 ml of ice water and 5 ml of acetic acid
  11. dry with materialThe organic phase was dried over magnesium sulfate
  12. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-da8421019ac54d7293fc156c9c05d6bb
Quelldatensatz
uspto-grants-1987_12
Patentnummer
US04713471

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