Potassium Carbonate → Methyl (4-hydroxymethyl-2-propylphenoxy)-2-phenylacetate

HRID 37236

Reaktionsgleichung

Reaktionsgleichung von HRID 37236
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[CH2:10][CH2:11][CH3:12].Br[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][C:21]([O:23][CH3:24])=[O:22].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[OH:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([O:1][CH:20]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:14]=2)[C:21]([O:23][CH3:24])=[O:22])=[C:3]([CH2:10][CH2:11][CH3:12])[CH:4]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 8063364Methyl 2-(2-bromophenyl)acetateHCID 220112094-(Hydroxymethyl)-2-propylphenol

Produkt 1

HCID 19802778Methyl (4-hydroxymethyl-2-propylphenoxy)-2-phenylacetateAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 0.484 g (2.91 mmol) of the product of Step F dissolved in 12 mL of acetone were added 0.667 g (2.91 mmol) of methyl 2-bromophenylacetate, 0.804 g (5.82 mmol) of anhydrous K2CO3 and the mixture was stirred and heated at reflux for 5 hours. The mixture was then cooled, filtered and evaporated in vacuo. The residual oil was purified on a silica gel flash chromatography column eluted with 30% ethyl acetate/hexane to afford 0.756 g (83%) of the title compound.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. temperatureThe mixture was then cooled
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residual oil was purified on a silica gel flash chromatography column
  7. washeluted with 30% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-5645db268bf14eb39b4994f9c8f658d7
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420133

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