Dimethylformamide → HCID 68291767, Verbindung

HRID 72999

Reaktionsgleichung

Reaktionsgleichung von HRID 72999
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[CH3:11].[C:12](=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH3:20].CN(C)[CH:23]=[O:24]>O.CCOCC>[CH2:19]([O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:24][CH2:23][CH3:12])=[O:8])=[CH:4][C:3]=1[CH3:11])[CH3:20]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 681384-Hydroxy-3-methylbenzoic acid

Produkt 1

HCID 68291767HCID 68291767, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

To a solution of 4-hydroxy-3-methyl-benzoic acid (1.00 g, 6.57 mmol) in N,N-dimethylformamide (10 mL) was added potassium carbonate (2.73 g, 19.7 mmol) and bromoethane (3.58 g, 2.44 mL, 32.9 mmol). The reaction mixture heated at 45° C. for 48 h in a sealed tube. The reaction mixture allowed to cool then diluted with water and ether. The ether layer was washed with 50% saturated NaHCO3 (50 mL) and brine (50 mL), dried over Na2SO4, and concentrated in vacuo to provide ethyl 4-ethoxy-3-methylbenzoate as an orange-colored oil. The crude product was taken directly to the next step. ESI-MS m/z calc. 208.10994. Found 209.3 (M+1)+; Retention time: 1.78 minutes (3 min run).

Aufarbeitung

  1. temperatureto cool
  2. washThe ether layer was washed with 50% saturated NaHCO3 (50 mL) and brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-618f5b7fd05b46789297afc7e800762d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828996B2

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