Water → 1-(2',4'-Dichloro-biphenyl-4-yl)-6-hydroxy-hexan-1-one

HRID 227892

Reaktionsgleichung

Reaktionsgleichung von HRID 227892
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:21])[CH2:16][CH2:17][CH2:18][CH:19]=[CH2:20])=[CH:11][CH:10]=1.B(O[O-])=[O:23].[Na+].O>B1C2CCCC1CCC2>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:21])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:23])=[CH:11][CH:10]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 517072Sodium PerborateHCID 577572631-(2',4'-Dichloro-biphenyl-4-yl)-hex-5-en-1-one

Produkt 1

HCID 248965951-(2',4'-Dichloro-biphenyl-4-yl)-6-hydroxy-hexan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 789669-Borabicyclo(3.3.1)nonaneLösungsmittel

Versuchsvorschrift

1-(2′,4′-Dichloro-biphenyl-4-yl)-hex-5-en-1-one (1.1 g) was dissolved in 0.5 M 9-BBN (6.9 mL) and stirred at room temperature for 4 hours. Sodium perborate (1 g) was added and the mixture stirred at room temperature for 1 hour. Water (3 mL) was added and the mixture stirred at 50° C. for 2 hours, then overnight at room temperature. The mixture was extracted with ether, dried, and evaporated to give an oil. The oil was purified by column chromatography to give an oil which solidified to a white amorphous solid on standing, and which was recrystallised from ether/petrol to give the title compound as a white powder. 13C NMR (CDCl3): δ23.9, 25.5, 32.5, 38.6, 62.7, 127.4, 128.0, 129.7, 129.9, 131.9, 133.1, 134.5, 136.3, 138.0, 142.8 and 199.9. 1H NMR (CDCl3): δ 1.45 (2H, m), 1.60 (2H, m), 1.80 (2H, m), 3.01 (2H, t, J=6.5 Hz), 3.68 (2H, t, J=6.5 Hz), 7.28 (2H, d, J=8.2 Hz), 7.30 (1H, s), 7.50 (2H, m) and 8.01 (2H, d, J=8.2 Hz).

Aufarbeitung

  1. stirringthe mixture stirred at room temperature for 1 hour
  2. stirringthe mixture stirred at 50° C. for 2 hours
  3. customovernight
  4. customat room temperature
  5. extractionThe mixture was extracted with ether
  6. customdried
  7. customevaporated
  8. customto give an oil
  9. customThe oil was purified by column chromatography
  10. customto give an oil which
  11. customwhich was recrystallised from ether/petrol

Quellen und Nachweise

ORD-Eintrag
ord-d12c44ba7bec4468944f2414095dda3a
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560597B2

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