2,6-Lutidine → 4-Decylbenzaldehyde

HRID 1492085노트

반응식

HRID 1492085 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

HCID 128390194-Decylbenzaldehyde수율 77.1%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3a2810ac3e08484f89bef926f7f15fa6
출처 데이터셋
uspto-grants-1994_12
특허 번호
US05371284

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