Suberic acid → Oct-4-enedioic acid

HRID 2264788

Reaktionsgleichung

Reaktionsgleichung von HRID 2264788
[C:1]([OH:12])(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9]>ClCCl>[C:1]([OH:12])(=[O:11])[CH2:2][CH2:3][CH:4]=[CH:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9]

Komponenten

3

Edukt 1

HCID 10457Suberic acid

Produkt 1

HCID 84313Oct-4-enedioic acidAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Intramolecular cyclic diester of octane-1,8-dioic acid and 2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethyl-phenol Grubbs catalyst (benzylidene-bis-(tricyclohexylphosphine)-dichlororuthenium, 16 mg, 0.002 mmol, 2 mol-%) was added to a solution of (±)-pent-4-enoic acid 2-(3-diisopropylamino-1-phenylpropyl)-4-(pent-4-enoyloxnymethyl)-phenyl ester (483 mg, 0.96 mmol) in dichloromethane (150 ml) and the mixture was refluxed for 96 hrs. under an atmosphere of nitrogen gas, after which all of the starting material was consumed as indicated by tlc. The mixture was filtered through a short pad of basic alumina, and the solvent was removed in vacuum. Flash chromatography (solvent system (4)) afforded the intermediate intramolecular cyclic diester of oct-4-ene-1,8-dioic acid and 2-(3-diisopropylamino)-1-(phenylpropyl)-4-hydroxymethyl-phenol (324 mg) as a colourless syrup (tlc: (4) Rf 0.68) in 71% yield, mixture of two geometrical isomers.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 96 hrs
  2. customunder an atmosphere of nitrogen gas, after which all of the starting material was consumed
  3. filtrationThe mixture was filtered through a short pad of basic alumina
  4. customthe solvent was removed in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f03fb88b04584948b9f4274e9d7d34a6
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855230B2

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