Methyl bromoacetate → 1,1-Bis-(4-hydroxyphenyl)-1-(4-methoxycarbonylmethoxyphenyl)ethane

HRID 510324

Reaktionsgleichung

Reaktionsgleichung von HRID 510324
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[OH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)[CH3:15])=[CH:10][CH:9]=1>[I-].[K+].CC(C)=O>[OH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:16]2[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=2)([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:2][C:3]([O:5][CH3:6])=[O:4])=[CH:25][CH:24]=2)[CH3:15])=[CH:10][CH:9]=1

Komponenten

5

Edukt 2

HCID 60984Methyl bromoacetateHCID 931181,1,1-Tris(4-hydroxyphenyl)ethane

Produkt 1

HCID 117178131,1-Bis-(4-hydroxyphenyl)-1-(4-methoxycarbonylmethoxyphenyl)ethaneAusbeute 85,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 4875Potassium IodideKatalysatorHCID 180AcetoneLösungsmittel

Versuchsvorschrift

Methyl bromoacetate (0.48 mL, 5 mmol) was added dropwise to an acetone solution (10 mL) including 1,1,1-tris(4-hydroxyphenyl)ethane (1.53 g, 5 mmol) potassium carbonate (0.79 g, 5 mmol) and potassium iodide (16 mg, 0.1 mmol). The addition was done at room temperature under argon. The mixture was refluxed for 24 h, and then it was cooled to room temperature and extracted with ethyl acetate. The combined organic layer was washed with 3% aqueous NaHCO3, a saturated brine solution, dried (Na2SO4) and then evaporated to dryness to give 1.61 g (85% yield) of the desired compound as a colorless semisolid. 1H-NMR (300 MHz, d6-DMSO): 1.96 [s, 3H, —CH3], 3.67 [s, 3H, —OCH3], 4.71 [s, 4H, —OCH2—], 6.57-6.64 [m, 4H, Ar—H], 6.72-6.81 [m, 6H, Ar—H], 6.85-6.92 [m, 2H, Ar—H].

Aufarbeitung

  1. additionThe addition
  2. customwas done at room temperature under argon
  3. temperatureThe mixture was refluxed for 24 h
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layer was washed with 3% aqueous NaHCO3
  6. dry with materiala saturated brine solution, dried (Na2SO4)
  7. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-bc0e8b82de0849fa90dc3c84ba4aec06
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096607B2

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