Oxalyl chloride → HCID 11041567, Verbindung

HRID 2292282Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2292282
[CH3:1][C@H:2]([CH2:7][CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:3][C:4](O)=[O:5].C(Cl)(=O)C([Cl:16])=O>C1C=CC=CC=1>[CH3:1][C@H:2]([CH2:7][CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:3][C:4]([Cl:16])=[O:5]

Komponenten

4

Edukt 2

HCID 65578Oxalyl chlorideHCID 13191833(R)-(+)-3,7-dimethyloctanoic acid

Produkt 1

HCID 11041567HCID 11041567, VerbindungAusbeute 95,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A solution of 11.37 g (66.1 mmoles) of (R)-(+)-3,7-dimethyloctanoic acid in 50 ml of benzene was stirred while 10 ml (114.6 mmoles) of oxalyl chloride was added. The solution was stirred and refluxed overnight then concentrated in vacuo giving 12.03 g (95.6%) of (R)-(+)-3,7-dimethyloctanoyl chloride as an oil. An 8.2 g (43.0 mmoles) sample of this material in 10 ml of dichloromethane was added to a stirred solution of 6.2 (43.0 mmoles) of Meldrum's Acid and 8.68 ml of pyridine in 40 ml of dichloromethane, at 0° C. The resulting solution was stirred overnight then treated with cold 3N aqueous HCl. The organic phase was separated and the aqueous phase was extracted with dichloromethane. The dichloromethane extracts were combined, dried (Na2SO4), and concentrated in vacuo giving 12.1 g of crude product. This material was dissolved in 100 ml of methanol and the solution was refluxed for 4 hr then cooled and concentrated in vacuo. The residue was chromatographed on silica gel giving (R)-5,9-dimethyl-3-oxodecanoic acid methyl ester as an oil, eluted with pet. ether-ether mixtures.

Aufarbeitung

  1. additionwas added
  2. temperaturerefluxed overnight
  3. concentrationthen concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a204b61b61a640698a85b1661e01de89
Quelldatensatz
uspto-grants-1989_01
Patentnummer
US04801724

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