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Hydrochloric Acid → 6-(Hydroxymethyl)-2-benzofuran-1(3H)-one

HRID 2080899
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2080899
C[O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([CH2:10]Br)[CH:7]=[CH:6][C:5]=1[CH2:12]Br.C(=O)([O-])[O-:16].[Ca+2].Cl>O1CCOCC1>[OH:16][CH2:10][C:8]1[CH:9]=[C:4]2[C:5]([CH2:12][O:2][C:3]2=[O:14])=[CH:6][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 10112Calcium CarbonateHCID 12633556Methyl 2,5-bis(bromomethyl)benzoate

Produkt 1

HCID 178625846-(Hydroxymethyl)-2-benzofuran-1(3H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

The compound (1.1274 g) obtained in Example 102-1 was dissolved in carbon tetrachloride (19.2 ml). The reaction solution was added with N-bromosuccinimide (2.417 g) and benzoyl peroxide (147.2 mg), and the whole was refluxed under heating for 6.5 hours. After having been cooled to room temperature, the reaction solution was concentrated under reduced pressure. The resultant residue was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining a mixture (2.4003 g) containing 2,5-bis-bromomethyl-benzoic acid methyl ester. The resultant mixture was dissolved in a 50% 1,4-dioxane aqueous solution (48 ml). The reaction solution was added with calcium carbonate (3.4823 g) and the whole was stirred at 100° C. for 16.5 hours. After having been cooled to room temperature, the reaction solution was cooled to 0° C. and concentrated hydrochloric acid was gradually added thereto to make the pH of the solution to 2. After that, the whole was stirred at room temperature for 20 minutes. The reaction solution was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution and then dried with anhydrous sodium sulfate. After the drying agent was filtrated out, the filtrate was concentrated under reduced pressure. The resultant residue was purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (372.0 mg) as a white crystal.

Aufarbeitung

  1. temperatureAfter having been cooled to room temperature
  2. temperaturethe reaction solution was cooled to 0° C.
  3. stirringAfter that, the whole was stirred at room temperature for 20 minutes
  4. extractionThe reaction solution was subjected to extraction with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution
  6. dry with materiala saturated saline solution and then dried with anhydrous sodium sulfate
  7. filtrationAfter the drying agent was filtrated out
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe resultant residue was purified through silica gel column chromatography (chloroform/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-dd8b359fd6704c9a804b253937db5d7d
Quelldatensatz
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07932281B2

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