Ammonium Chloride → Methyl 2-methoxymethylphenylglyoxylate

HRID 36603

Reaktionsgleichung

Reaktionsgleichung von HRID 36603
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][O:10][CH3:11].[Cl-].[CH3:13][O:14][C:15](=[O:19])[C:16](O)=[O:17].[Cl-].[NH4+]>C1COCC1.[Cl-].[Zn+2].[Cl-]>[CH3:11][O:10][CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:16](=[O:17])[C:15]([O:14][CH3:13])=[O:19]

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 129271621-Bromo-2-(methoxymethyl)benzeneHCID 86640482Oxalic acid monomethyl ester chloride

Produkt 1

HCID 19937173Methyl 2-methoxymethylphenylglyoxylateAusbeute 57,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

500 ml of an ethereal 1 M zinc chloride solution was dripped into a Grignard solution prepared from 12.0 g (0.46 mol) of magnesium shavings and 99.5 g (0.5 mol) of 1-bromo-2-methoxymethylbenzene in 500 ml of THF. The mixture was then refluxed for 1 hour, and a solution of 61.2 g (0.5 mol) of oxalic acid methyl ester chloride in 100 ml of THF was dripped in at an internal temperature of (-10)° C. After the mixture had been heated to about 20° C. it was stirred for a further 20 hours and then hydrolyzed with saturated ammonium chloride solution. After extraction with ether the combined ether phases were washed with water, dried and evaporated down. There was obtained 60 g of product (57.7%) as a mobile liquid.

Aufarbeitung

  1. temperatureThe mixture was then refluxed for 1 hour
  2. extractionAfter extraction with ether the combined ether phases
  3. washwere washed with water
  4. customdried
  5. customevaporated down

Quellen und Nachweise

ORD-Eintrag
ord-5953b0e084ff4fe593745937720da0a3
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05416068

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