Water → 3-Undecylphenol

HRID 1779404

반응식

HRID 1779404 반응식
C1(C[O:8][C:9]2[CH:10]=[C:11]([CH:15](O)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:12]=[CH:13][CH:14]=2)C=CC=CC=1.O>[Pd].C(O)C.C(O)(=O)C>[CH2:15]([C:11]1[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][CH:12]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

참가 물질

6

반응물 2

HCID 962WaterHCID 199554661-(3-(Phenylmethoxy)phenyl]undecanol2회

생성물 1

HCID 232748073-Undecylphenol수율 387.5%

시약·촉매·용매 3

HCID 23938Palladium촉매2회HCID 176Acetic Acid용매2회HCID 702Ethanol용매2회

실험 절차

A mixture of 3.0 grams (0.008 mole) of 1-(3-(phenylmethoxy) phenyl]undecanol and 0.5 gram (catalyst) of 10% palladium on charcoal and 50 mL of acetic acid in 50 mL of ethanol was hydrogenated using a Parr hydrogenator. Upon the uptake of the theoretical amount of hydrogen, the reaction mixture was filtered and concentrated under reduced pressure to a residual oil. NMR analysis of the oil indicated that the phenol portion of the molecule was completely unprotected, and the benzylic hydroxyl was about 70% removed. The oil was then mixed with-16.5 grams (0.047 mole) of 1-[3-(phenylmethoxy)phenyl]undecanol, 2.0 grams of 1.0% palladium on charcoal, 10 mL of water, and 50 mL of ethanol in 130 mL of acetic acid. The mixture was then hydrogenated as previously described, using the Parr hydrogenator. The reaction mixture was filtered and concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel. Elution was accomplished using 9:1 petroleum ether and diethyl ether and 8:2 petroleum ether and diethyl ether. The product-containing fractions were combined and concentrated under reduced pressure, yielding 7.7 grams of 3-undecylphenol. The NMR spectrum was consistent with the proposed structure.

후처리

  1. filtrationUpon the uptake of the theoretical amount of hydrogen, the reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure to a residual oil
  3. customremoved
  4. filtrationThe reaction mixture was filtered
  5. concentrationconcentrated under reduced pressure to a residue
  6. washElution
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-c5a731d7addc4a1696dcd3b88c88869e
출처 데이터셋
uspto-grants-1997_05
특허 번호
US05627189

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