Heptane → 2-Isobutyryl-3-methyl-benzoic acid

HRID 1047847Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1047847
Br[C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CCCCCCC.[Li]CCCC.CCCCCC.[C:30](Cl)(=[O:34])[CH:31]([CH3:33])[CH3:32]>C1COCC1>[C:30]([C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])(=[O:34])[CH:31]([CH3:33])[CH3:32]

Komponenten

6

Edukt 4

HCID 8900HeptaneHCID 62325Isobutyryl chlorideHCID 27355882-Bromo-3-methylbenzoic acidHCID 178418244HCID 178418244, Verbindung

Produkt 1

HCID 593141812-Isobutyryl-3-methyl-benzoic acidAusbeute 58,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The solution of 2-bromo-3-methyl-benzoic acid (1.5 g, 6.98 mmol) in 10 mL THF is treated with 1M Bu2Mg/heptane at −15° C. under argon. After stirring for 30 min, 1.6M n-BuLi/hexane is added dropwise at −15° C. and the mixture is left for 1 hr. Then isobutyryl chloride (2.95 ml, 27.9 mmol) is added dropwise. After another 30 min stirring, the reaction is quenched with 2N HCl aqueous solution (2 ml). After concentration, the residue is purified by HPLC to give a pure product (227) as white solid (840 mg, 58%).

Aufarbeitung

  1. waitthe mixture is left for 1 hr
  2. stirringAfter another 30 min stirring
  3. customthe reaction is quenched with 2N HCl aqueous solution (2 ml)
  4. concentrationAfter concentration
  5. customthe residue is purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-836175aee40d4ca8b4f4541a62143c4f
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569535B2

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