2,6-Lutidine → 4-Decylbenzaldehyde

HRID 1492085Notes

Reaction equation

HRID 1492085 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

HCID 128390194-DecylbenzaldehydeYield 77.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-3a2810ac3e08484f89bef926f7f15fa6
Source dataset
uspto-grants-1994_12
Patent number
US05371284

Reaction notes

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