Sodium Iodide → Benzyl 3-chloro-5-(3-hydroxypropoxy)benzoate

HRID 1698859Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1698859
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([OH:18])[CH:17]=1)[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:26][CH2:27][CH2:28][OH:29].[I-].[Na+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([O:18][CH2:26][CH2:27][CH2:28][OH:29])[CH:17]=1)[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 10796Cesium carbonate3×HCID 123083-Bromo-1-propanol2×HCID 18322181Benzyl 3-chloro-5-hydroxybenzoate

Produkt 1

HCID 18322176Benzyl 3-chloro-5-(3-hydroxypropoxy)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of phenol 25 (8.80 g, 33.0 mmol) and 3-bromno-1-propanol (2.9 mL, 33 mmol) in acetonitrile (300 nL) was added solid cesium carbonate (12 g, 37 mmol). After stirring 16hrs at 50° C., more 3-bromo-1-propanol (3.3 mmol) and cesium carbonate (3.3 mmol) were added and the reaction stirred another 2 hrs. After adding more 3-bromo-1-propanol and cesium carbonate (3.3 mmol each) and sodium iodide (3.3 mmol), the reaction was stirred 30 minutes at 65° C., then cooled and filtered. The filtrate was evaporated in vacuo, the residue dissolved in ethyl acetate, washed with water, and the organic layer dried over Na2SO4 and filtered. The evaporated filtrate then gave product 26 (5.96 g 56%). 1H NMR (300 MHz, CDCl3) δ 7.63 (t, 1H, J=1.5 Hz), 7.48 (dd, 1H, J=2.4 Hz, 1.4 Hz), 7.46-7.31 (m, 5H), 7.09 (t, 1H, J=2.4 Hz), 5.35 (s, 2H), 4.14 (t, 2H, J =6.0 Hz), 3.85 (t, 2H, J=6.0 Hz), 2.05 (pentet, 2H, J=6.0 Hz).

Aufarbeitung

  1. stirringthe reaction stirred another 2 hrs
  2. stirringthe reaction was stirred 30 minutes at 65° C.
  3. temperaturecooled
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. dissolutionthe residue dissolved in ethyl acetate
  7. washwashed with water
  8. dry with materialthe organic layer dried over Na2SO4
  9. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-1296ac4b59674eb2b02118fe501f2986
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06344466B2

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