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Water → 4-Benzyloxy-3-cyclopentyloxybenzaldehyde

HRID 1489716
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1489716
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[OH:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:24]1(Br)[CH2:28][CH2:27][CH2:26][CH2:25]1.O>CN(C)C=O.C(OCC)C>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[O:17][CH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 5613694-Benzyloxy-3-hydroxybenzaldehyde

Produkt 1

HCID 211878994-Benzyloxy-3-cyclopentyloxybenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl Ether
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A stirred solution of 4-benzyloxy-3-hydroxybenzaldehyde (60.9 g; that is prepared as described in Reference Example 36) in dry dimethylformamide (270 mL) under nitrogen is treated portionwise with potassium carbonate (79.5 g). After stirring at room temperature for 45 minutes, it is treated with cyclopentyl bromide (34.3 mL), and the resulting suspension is heated at 60° C. for 8 hours. After cooling, the solution is evaporated to low bulk under reduced pressure, to give an oil. This oil is treated with water (250 mL) and diethyl ether (300 mL), and the aqueous layer is washed with further quantities of diethyl ether (2×50 mL). The combined ethereal extracts are washed with brine (1×50 mL) and with water (3×50 mL), dried over magnesium sulfate and evaporated. The resulting residue is crystallized from methanol, to give 4-benzyloxy-3-cyclopentyloxybenzaldehyde (79 g), m.p. 55°-56° C. [Elemental analysis: C,77.1; H,6.9%; calculated: C,77.0; H,6.8%].

Aufarbeitung

  1. customthat is prepared
  2. temperaturethe resulting suspension is heated at 60° C. for 8 hours
  3. temperatureAfter cooling
  4. customthe solution is evaporated to low bulk under reduced pressure
  5. customto give an oil
  6. washthe aqueous layer is washed with further quantities of diethyl ether (2×50 mL)
  7. washThe combined ethereal extracts are washed with brine (1×50 mL) and with water (3×50 mL)
  8. dry with materialdried over magnesium sulfate
  9. customevaporated
  10. customThe resulting residue is crystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-51c0c0481bc5468291ecbb4180212a49
Quelldatensatz
uspto-grants-1997_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05679696

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