Methyl formate → Methyl alpha-[2-(4-phenoxybut-1-yloxy)-phenyl]-beta-hydroxyacrylate

HRID 1085337

Reaktionsgleichung

Reaktionsgleichung von HRID 1085337
[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:24](OC)=[O:25].[H-].[Na+]>C(OCC)C>[O:1]([CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19](=[CH:24][OH:25])[C:20]([O:22][CH3:23])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 7865Methyl formateHCID 24758Sodium hydrideHCID 14550847Methyl 2-(4-phenoxybut-1-yloxy)-phenylacetate

Produkt 1

HCID 67930312Methyl alpha-[2-(4-phenoxybut-1-yloxy)-phenyl]-beta-hydroxyacrylateAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A mixture of 30 g (0.10 mole) of methyl 2-(4-phenoxybut-1-yloxy)-phenylacetate, 12.5 g (0.21 mole) of methyl formate and 100 ml of diethyl ether is added dropwise at room temperature to a suspension of 3.4 g (0.14 mole) of sodium hydride in 50 ml of diethyl ether. The mixture is stirred for 12 hours at room temperature and is then hydrolyzed by adding ice. The aqueous, alkaline phase is extracted with diethyl ether, acidified with dilute HCl and again extracted by shaking with diethyl ether. After the organic phase has been evaporated down, 21 g (71%) of methyl alpha-[2-(4-phenoxybut-1-yloxy)-phenyl]-β-hydroxyacrylate are obtained.

Aufarbeitung

  1. additionby adding ice
  2. extractionThe aqueous, alkaline phase is extracted with diethyl ether
  3. extractionagain extracted
  4. stirringby shaking with diethyl ether
  5. customAfter the organic phase has been evaporated down

Quellen und Nachweise

ORD-Eintrag
ord-1dd187cc3bf24b67b01ec4697ffcf142
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05008438

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