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Water → Methyl 4-[(acetyloxy)methyl]-3-methylbenzoate

HRID 501803
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 501803
[C:1]([O:4][CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]=1Br)(=[O:3])[CH3:2].O.[CH2:18](OCC)C>CN(C)P(N(C)C)(N(C)C)=O.C[Sn](C)(C)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:4][CH2:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][C:7]=1[CH3:18])(=[O:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 962WaterHCID 3283Diethyl EtherHCID 57543439Methyl 4-[(acetyloxy)methyl]-3-bromobenzoate

Produkt 1

HCID 68460449Methyl 4-[(acetyloxy)methyl]-3-methylbenzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysator
HCID 11661
Tetramethyltin
Lösungsmittel
HCID 12679HexamethylphosphoramideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

5.30 g of methyl 4-[(acetyloxy)methyl]-3-bromobenzoate was dissolved in 50 mL of hexamethylphosphoramide, to which 6.6 mL of tetramethyltin and 0.26 g of bis(triphenylphosphine)-palladium(II) dichloride were added at room temperature in a stream of nitrogen, and this solution was stirred for 3 hours at 70° C. The reaction mixture was cooled to room temperature, and was added to a mixture of water and diethyl ether, and then the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1] to yield 4.17 g of methyl 4-[(acetyloxy)methyl]-3-methylbenzoate as brown oil.

Aufarbeitung

  1. additionwere added at room temperature in a stream of nitrogen
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customthe organic phase was separated
  4. washAfter the resultant organic phase was washed with water
  5. dry with materiala saturated sodium chloride solution, the washed phase was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled out under reduced pressure
  7. customThe resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1]

Quellen und Nachweise

ORD-Eintrag
ord-306d33e6cdb64af592d0789d16344254
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07772285B2

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