2,6-Lutidine → 4-Decylbenzaldehyde

HRID 1492085Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1492085
[CH2:1]([C:11]1[CH:19]=[CH:18][C:14]([C:15](Cl)=[O:16])=[CH:13][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].N1C(C)=CC=CC=1C>[Pd].O1CCCC1>[CH2:1]([C:11]1[CH:12]=[CH:13][C:14]([CH:15]=[O:16])=[CH:18][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Komponenten

5

Edukt 2

HCID 79372,6-LutidineHCID 104714Benzoyl chloride, 4-decyl-

Produkt 1

HCID 128390194-DecylbenzaldehydeAusbeute 77,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Rosenmund Reduction--Hydrogenate a mixture of 4-(n-decyl)benzoyl chloride (28 g., 0.1 mol), 10% palladium on carbon (2 g.), 2,6-lutidine (10.9 g., dried over KOH and distilled), and tetrahydrofuran (THF) (300 ml., distilled from LiAlH4) in a Paar apparatus for 30 min. at 25° C. under an H2 atmosphere (62 psi). Filter the resulting mixture and collect the catalyst. Wash the catalyst with THF. Evaporate the filtrate and partition the residue between diethyl ether and H2O. Wash the combined organic solutions with aqueous HCl (0.1N) and NaHCO3 (0.1N) solutions. Evaporate the solvent from the dried organic solution to give a liquid. Distill the liquid to give 4-(n-decyl)benzaldehyde (19 g. 77% yield, b.p. 152°-156° C. at 0.3 mm).

Aufarbeitung

  1. filtrationFilter the resulting mixture
  2. customcollect the catalyst
  3. washWash the catalyst with THF
  4. customEvaporate the filtrate
  5. custompartition the residue between diethyl ether and H2O
  6. washWash the combined organic solutions with aqueous HCl (0.1N) and NaHCO3 (0.1N) solutions
  7. customEvaporate the solvent from the dried organic solution
  8. customto give a liquid
  9. distillationDistill the liquid

Quellen und Nachweise

ORD-Eintrag
ord-3a2810ac3e08484f89bef926f7f15fa6
Quelldatensatz
uspto-grants-1994_12
Patentnummer
US05371284

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