Allyl bromide → Methyl 2-hydroxy-4-[(prop-2-en-1-yl)oxy]benzoate

HRID 29643

Reaktionsgleichung

Reaktionsgleichung von HRID 29643
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[CH:20]=[CH2:21]>CC(C)=O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:21][CH:20]=[CH2:19])=[CH:6][C:5]=1[OH:11]

Komponenten

5

Edukt 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 16523Methyl 2,4-Dihydroxybenzoate

Produkt 1

HCID 13019278Methyl 2-hydroxy-4-[(prop-2-en-1-yl)oxy]benzoateAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 2,4-dihydroxy-benzoic acid methyl ester (12.254 g, 72.8 mmol) in acetone (120 mL) was added potassium carbonate (30.72 g, 222.3 mmol) and allyl bromide (7 mL, 80.9 mmol). The reaction mixture was heated at reflux for 5 hours, and then cooled to room temperature. It was partitioned between ethyl acetate and brine and the aqueous layer was extracted with ethyl acetate. The combined organics were washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography using ethyl acetate/hexanes (4/96) to afford 4-allyloxy-2-hydroxy-benzoic acid methyl ester (10.952 g, 77%) as a yellow oil. 1H NMR (300 MHz, CDCl3); δ 10.95 (s, 1H), 7.72 (d, 2H), 6.45 (m, 2H), 6.02 (m, 1H), 5.35 (m, 2H), 4.55 (d, 2H), 3.90 (s, 3H).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 5 hours
  3. customIt was partitioned between ethyl acetate and brine
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organics were washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7fced78c4df249e9ac3f703c112a78d0
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420083B2

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