Allyl bromide → 1-Chloro-3-phenylhex-5-en-3-ol

HRID 333890

Reaktionsgleichung

Reaktionsgleichung von HRID 333890
[Cl:1][CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[NH4+].[Cl-].[CH2:14](Br)[CH:15]=[CH2:16]>C1COCC1.[Zn]>[Cl:1][CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([OH:5])[CH2:16][CH:15]=[CH2:14]

Komponenten

6

Edukt 3

HCID 7841Allyl bromideHCID 25517Ammonium ChlorideHCID 702953-Chloropropiophenone

Produkt 1

HCID 159334751-Chloro-3-phenylhex-5-en-3-olAusbeute 97,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

A solution of 3-chloro-1-phenylpropan-1-one (100 g, 0.595 mol) in THF (280 ml) was added dropwise to a well-stirred mixture of zinc powder (need not be activated) (40 g, 1.231 mol, satd aq NH4Cl solution (1500 ml) and THF (400 ml). Allyl bromide (143 g, 1.19 mol) was dissolved in THF (200 ml) was slowly added to the reaction mixture. The reaction was mildly exothermic, and the mixture began to reflux spontaneously. After refluxing had ceased, the mixture was stirred for 1 h. The mixture was extracted with EtOAc, dried over anhydrous Na2SO4, and concentrated to give 1-chloro-3-phenylhex-5-en-3-ol (122 g, 97%). 1H NMR: (400 MHz, CDCl3): δ=2.24 (s, 1H), 2.34 (m, 2H), 2.53 (m, 1H), 2.75 (m, 1H), 3.20 (m, 1H), 3.58 (m, 1H), 5.18 (t, 1H), 5.51 (m, 1H), 7.26 (m, 1H), 7.26-7.39 (m, 3H).

Aufarbeitung

  1. additionwas slowly added to the reaction mixture
  2. temperatureto reflux spontaneously
  3. temperatureAfter refluxing
  4. extractionThe mixture was extracted with EtOAc
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-62322239fe214a53b55df36564a28d4a
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883778B2

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