Carbon Dioxide → 3.5-Diethyl-4-methoxybenzoic acid

HRID 1280923Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1280923
Br[C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[C:5]([O:10][CH3:11])=[C:4]([CH2:12][CH3:13])[CH:3]=1.C([Li])CCC.[C:19](=[O:21])=[O:20]>C1COCC1.CCOC(C)=O>[CH2:12]([C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([CH2:8][CH3:9])[C:5]=1[O:10][CH3:11])[C:19]([OH:21])=[O:20])[CH3:13]

Komponenten

6

Edukt 3

HCID 280Carbon DioxideHCID 234456364-Bromo-2,6-diethylanisoleHCID 178418339Butyllithium

Produkt 1

HCID 234456633.5-Diethyl-4-methoxybenzoic acidAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

At −78° C., to a stirred solution of 4-bromo-2,6-diethylanisole (12.0 g, 49.4 mmol) in THF (329 mL) was added dropwise n-butyllithium (27.2 mL, 43.5 mmol). After 3h, the reaction was poured into crushed dry ice and allowed to warm to ambient temperature. The reaction mixture was diluted with EtOAc, concentrated, suspended in H2O, acidified (pH 1), filtered and the collected solids washed with H2O. The crude product was slurried in hexane (15 mL), collected by filtration and dried to give 6.76 g (66%) of the title compound. 1H NMR: consistent. IR (KBr) consistent. mass spectrum (EI), m/z 208 (M+). Anal. Calcd. for C12H16O3: C, 69.21; H, 7.74; N, 0.00. Found: C, 69.28; H, 7.49; N, 0.07.

Aufarbeitung

  1. concentrationconcentrated
  2. filtrationfiltered
  3. washthe collected solids washed with H2O
  4. filtrationcollected by filtration
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-e3c8481213fe4d79a6a2015c8e1d7e4c
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06451845B1

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