Diethyl Ether → Methyl 2-[p-(benzyloxy)phenoxy]propionate

HRID 64584

Reaktionsgleichung

Reaktionsgleichung von HRID 64584
Br[CH:2]([CH3:7])[C:3]([O:5][CH3:6])=[O:4].[Na].[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CCOCC>CN(C=O)C>[CH2:9]([O:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][CH:2]([CH3:7])[C:3]([O:5][CH3:6])=[O:4])=[CH:21][CH:22]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 7638MonobenzoneHCID 95576Methyl 2-bromopropionateHCID 5360545Sodium

Produkt 1

HCID 13093988Methyl 2-[p-(benzyloxy)phenoxy]propionate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A 42 g (0.25 mole) portion of methyl 2-bromopropionate was added to 0.25 mole of the sodium salt of p-benzyloxyphenol (prepared from 13.5 g sodium methoxide and 50 g p-benzyloxyphenoxy) in 70 cc of DMF. The reaction mixture was heated at approximately 80° C. for 14.5 hours. The cooled reaction mixture was then poured into 1 liter ice-water. The product was isolated by ether extraction and was crystallized from methanol to give 45.2 g methyl 2-(4-benzyloxyphenoxy)propanoate, m.p. 38°-42°.

Aufarbeitung

  1. customThe cooled reaction mixture
  2. customwas crystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-66bb2d2a00534e9c92b4ff15626c6f80
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04609396

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