Hydrochloric Acid → Methyl 3-[4-(4-pentylphenyl)phenyl]acrylate

HRID 1386580Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1386580
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:19]([O:23][CH3:24])(=[O:22])[CH:20]=[CH2:21].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Cl>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O>[CH2:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([CH:21]=[CH:20][C:19]([O:23][CH3:24])=[O:22])=[CH:3][CH:4]=2)=[CH:9][CH:10]=1)[CH2:15][CH2:16][CH2:17][CH3:18]

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 7294Methyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 6187094-Bromo-4'-pentylbiphenyl

Produkt 1

HCID 54407370Methyl 3-[4-(4-pentylphenyl)phenyl]acrylate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 4-bromo-4′-pentylbiphenyl (5.0 g), methyl acrylate (2.2 ml), palladium acetate (0.11 g) and tris(o-tolyl)phosphine (0.60 g) in triethylamine (16 ml) was refluxed for 15 hours under nitrogen atmosphere. The reaction mixture was poured into a mixture of cold water and ethyl acetate, and adjusted to about pH 1.5 with 6N hydrochloric acid. The separated organic layer was washed in turn with water and brine, and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give a crude powder, which was subjected to column chromatography on silica gel (200 ml), and eluted with a mixture of (n-hexane:ethyl acetate=100:0-94:6, V/V) to give Methyl 3-[4-(4-pentylphenyl)phenyl]acrylate (4.48 g).

Aufarbeitung

  1. temperaturewas refluxed for 15 hours under nitrogen atmosphere
  2. washThe separated organic layer was washed in turn with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe magnesium sulfate was filtered off
  5. customthe filtrate was evaporated under reduced pressure
  6. customto give a crude powder, which
  7. washeluted with a mixture of (n-hexane:ethyl acetate=100:0-94:6, V/V)

Quellen und Nachweise

ORD-Eintrag
ord-f055f41a22674cd1a50d461cc05f6980
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06265536B1

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