Hydrochloric Acid → 4-(Methoxymethoxymethyl)-2-methylbenzaldehyde

HRID 501792Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 501792
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][CH2:10][O:11][CH3:12])=[CH:4][C:3]=1[CH3:13].CN(C)[CH:16]=[O:17].O.Cl>O1CCCC1.C([Li])CCC.CCCCCC>[CH3:12][O:11][CH2:10][O:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH:16]=[O:17])=[C:3]([CH3:13])[CH:4]=1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6228DimethylformamideHCID 684578621-Bromo-4-((methoxymethoxy)methyl)-2-methylbenzene

Produkt 1

HCID 230215454-(Methoxymethoxymethyl)-2-methylbenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittelHCID 178418339ButyllithiumLösungsmittel

Reaktionsbedingungen

Temperatur
-65 °C

Versuchsvorschrift

4.00 g of 1-bromo-4-[(methoxymethoxy)methyl]-2-methylbenzene was dissolved in 40 mL of tetrahydrofuran, to which 11.5 mL of a solution of n-butyllithium in n-hexane (1.56 M) was added dropwise at −65 to −60° C., and then this mixture was stirred for 30 minutes at −65° C. Then, 20 mL of N,N-dimethylformamide was added dropwise thereto at −65 to −40° C., and a temperature of this reaction mixture was raised to room temperature over one hour and was stirred for another one hour at room temperature. Water was added to the reaction mixture and adjusted to pH 5 with 6M hydrochloric acid, followed by addition thereto of ethyl acetate, and then the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, 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 1.54 g of 4-[(methoxymethoxy)methyl]-2-methylbenzaldehyde as colorless oil.

Aufarbeitung

  1. additionwas added dropwise at −65 to −60° C.
  2. temperatureat −65 to −40° C., and a temperature of this reaction mixture was raised to room temperature over one hour
  3. stirringwas stirred for another one hour at room temperature
  4. additionfollowed by addition
  5. customof ethyl acetate, and then the organic phase was separated
  6. washAfter the resultant organic phase was washed with water
  7. dry with materiala saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled out under reduced pressure
  9. customThe resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1]

Quellen und Nachweise

ORD-Eintrag
ord-e4c1dba4962a48189a403b9116c41837
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772285B2

Notizen zur Reaktion

Wird geladen…