StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Dimethyl Sulfoxide → Methanone, [2-hydroxy-4-(3-hydroxypropoxy)phenyl]phenyl-

HRID 1862182
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1862182
[OH:1][C:2]1[CH:15]=[C:14]([OH:16])[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].Cl[CH:18]([OH:21])[CH2:19][CH3:20].C(=O)([O-])[O-].[K+].[K+].CS(C)=O>[I-].[K+].O>[OH:1][C:2]1[CH:15]=[C:14]([O:16][CH2:20][CH2:19][CH2:18][OH:21])[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 85722,4-DihydroxybenzophenoneHCID 11430Potassium CarbonateHCID 151098631-Chloropropan-1-ol

Produkt 1

HCID 10945581Methanone, [2-hydroxy-4-(3-hydroxypropoxy)phenyl]phenyl-Ausbeute 76,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 4875
Potassium Iodide
Katalysator
HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

To a 250 mL 3-necked round-bottom flask equipped with a magnetic stirrer was charged 20 g (93.5 mmol) of 2,4-dihydroxybenzophenone, 8.8 g (93.5 mmol) of chloropropanol, 100 mg (0.6 mmol) of potassium iodide, 12.92 g (93.5 mmol) of potassium carbonate, and 100 mL of dimethyl sulfoxide. The flask was immersed in an oil bath and the mixture heated at a bath temperature of 125° C. for 14 hours. The mixture was poured into 1.4 L of water and extracted with four 500 mL portions of methylene chloride. The combined organic extracts were washed with five 1200 in L portions of water, followed by two 2 L portions of 0.025% aqueous NaOH, and another 1.2 L portion of water. The organic layer was dried (MgSO4), filtered through Celite, and concentrated, leaving 19.4 g of product as a yellow solid. 1H NMR (CDCl3): δ12.58 (s, 1H, ArOH); 7.60-7.35 (m, 6H, Ar—H); 6.45-6.30 (m, 2H, Ar—H); 4.10 (t, 2H, Ar—O—CH2—); 3.79 (t, 2H, H—O—CH2—); 1.99 (m, 2H, —CH2—CH2—CH2—).

Aufarbeitung

  1. customTo a 250 mL 3-necked round-bottom flask equipped with a magnetic stirrer
  2. customThe flask was immersed in an oil bath
  3. extractionextracted with four 500 mL portions of methylene chloride
  4. washThe combined organic extracts were washed with five 1200 in L portions of water
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered through Celite
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2d99d51e0dd14ad8bc03383d2d551250
Quelldatensatz
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06537670B1

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion