Formaldehyde → 4-Ethyl-2-hydroxybenzaldehyde

HRID 343281

Reaktionsgleichung

Reaktionsgleichung von HRID 343281
C([Mg]Br)C.[CH2:5]([C:7]1[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=1)[CH3:6].[CH2:14]=[O:15].CN(C)P(N(C)C)(N(C)C)=O>O1CCCC1.C1(C)C=CC=CC=1>[CH2:5]([C:7]1[CH:12]=[CH:11][C:10]([CH:14]=[O:15])=[C:9]([OH:13])[CH:8]=1)[CH3:6]

Komponenten

7

Edukt 4

HCID 712FormaldehydeHCID 121013-EthylphenolHCID 12679HexamethylphosphoramideHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 102360174-Ethyl-2-hydroxybenzaldehydeAusbeute 69,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A stirred solution of 200 mL (0.20 mole) of 1.0M of ethylmagnesium bromide (in tetrahydrofuran) in 100 mL of tetrahydrofuran was cooled in an ice-bath and 25.0 grams (0.21 mole) of 3-ethylphenol was added dropwise. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature where it stirred for 30 minutes. After this time, 15.4 grams (0.51 mole) of paraformaldehyde, 36.7 grams (0.21 mole) of hexamethylphosphoramide, and 350 mL of toluene were added. Upon completion of addition, the reaction mixture was heated to 80° C. where it stirred for about 18 hours. The reaction mixture was then cooled and concentrated under reduced pressure to a residue. The residue was taken up in diethyl ether and 200 mL of an aqueous 10% hydrochloric acid solution was added. The aqueous layer was separated and extracted with diethyl ether. The extract was combined with the organic layer, and the combination was washed with water. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduce pressure to a residue. The residue was subjected to column chromatography on silica gel, using 1:1 hexane and methylene chloride as the eluant. The product-containing fractions were combined and concentrated under reduced pressure, yielding 21.8 grams of 5-ethyl-2-formylphenol. The NMR spectrum was consistent with the proposed structure.

Aufarbeitung

  1. additionUpon completion of addition
  2. additionUpon completion of addition
  3. temperaturethe reaction mixture was heated to 80° C. where it
  4. stirringstirred for about 18 hours
  5. temperatureThe reaction mixture was then cooled
  6. concentrationconcentrated under reduced pressure to a residue
  7. addition200 mL of an aqueous 10% hydrochloric acid solution was added
  8. customThe aqueous layer was separated
  9. extractionextracted with diethyl ether
  10. washthe combination was washed with water
  11. dry with materialThe organic layer was dried with magnesium sulfate
  12. filtrationfiltered
  13. concentrationThe filtrate was concentrated
  14. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b707ed1977ce42ceb5dcd42e9d14fa47
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05861359

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