2,6-Lutidine → 4-Decylbenzaldehyde

HRID 1492085ノート

反応式

HRID 1492085 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 128390194-Decylbenzaldehyde収率 77.1%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3a2810ac3e08484f89bef926f7f15fa6
出典データセット
uspto-grants-1994_12
特許番号
US05371284

反応ノート

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