4-Methyloxybenzyl chloride → 4-Methoxybenzyl 2,2-dimethyl-4-pentenoate

HRID 489009

Reaktionsgleichung

Reaktionsgleichung von HRID 489009
[CH3:1][C:2]([CH3:9])([CH2:6][CH:7]=[CH2:8])[C:3]([OH:5])=[O:4].CC(C)([O-])C.[K+].[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Cl)=[CH:20][CH:19]=1>CN(C=O)C>[CH3:1][C:2]([CH3:9])([CH2:6][CH:7]=[CH2:8])[C:3]([O:5][CH2:22][C:21]1[CH:24]=[CH:25][C:18]([O:17][CH3:16])=[CH:19][CH:20]=1)=[O:4]

Komponenten

5

Edukt 3

HCID 699934-Methyloxybenzyl chlorideHCID 1400652,2-Dimethyl-4-pentenoic acidHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 153113494-Methoxybenzyl 2,2-dimethyl-4-pentenoateAusbeute 95,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 2,2-dimethyl4-pentenoic acid (11.5 g, 90 mmol) in DMF (250 mL) at room temperature, was added potassium tert-butoxide (11.1 g, 99 mmol). The reaction mixture was stirred at 60° C. for 1 h. 4-Methoxybenzyl chloride (16.9 g, 108 mmol) was added and the reaction mixture was stirred at 60° C. for 4 h. The DMF was evaporated under vacuum, the residue was dissolved in ether (500 mL) and washed with water (3×200 mL). The organic phase was dried with Na2SO4 and evaporated to give 21.4 g of 4-methoxybenzyl 2,2-dimethyl-4-pentenoate.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at 60° C. for 4 h
  2. customThe DMF was evaporated under vacuum
  3. dissolutionthe residue was dissolved in ether (500 mL)
  4. washwashed with water (3×200 mL)
  5. dry with materialThe organic phase was dried with Na2SO4
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-7b8daaa9868f4be490c9452ae2bd74ef
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06974802B2

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