1,4-Dihydro-2-methylbenzoic acid → 2-Methylbenzoic acid

HRID 2396553

Reaktionsgleichung

Reaktionsgleichung von HRID 2396553
[CH3:1][C:2]1[CH:3]([CH:7]=[CH:8][CH2:9][CH:10]=1)[C:4]([OH:6])=[O:5]>C1C2C(CCCC2)CCC1.CCCCCC>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Komponenten

5

Edukt 2

HCID 5645811,4-Dihydro-2-methylbenzoic acidHCID 178527255HCID 178527255, Verbindung

Produkt 1

HCID 83732-Methylbenzoic acidAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7044DecalinLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a suspension of 2-methyl-l,4-dihydrobenzoic acid (0.085 g, 0.50 mmol; 81% pure, from Aldrich Chemical Company) in decalin (5 mL) under a nitrogen atmosphere was added the polysiloxane matrix material containing a homogeneous dispersion of metal particles (0.100 g as prepared according to Example 1). The solution was heated to reflux for 19 hours. On cooling the reaction mixture was diluted with hexane (25 mL) and extracted with aqueous sodium hydroxide (5%) solution (2×5 mL). The basic aqueous solution was acidified and extracted with chloroform (3×4 mL). The combined organic layer was dried over anhydrous sodium sulfate. Removal of solvent on rotary evaporator gave 2-methylbenzoic acid (0.065 g. 96%). IR(KBr) 3600-2000 (br), 2923, 1694, 1300, 920,731 cm-1. 1H NMR (300 MHz, CDCl3) δ 8.03 (ddd, J=8.5, 3.0, 1.5 Hz, 1 H), 7.42 (td, J=8.5, 1.5 Hz, 1H), 7.26 (td, J=8.5, 1.5 Hz, 1 H), 7.22 (dd, J=8.5, 1.5 Hz, 1 H), 2.64 (s, 3H).

Aufarbeitung

  1. additioncontaining
  2. customa homogeneous dispersion of metal particles (0.100 g as prepared according to Example 1)
  3. temperatureThe solution was heated
  4. temperatureto reflux for 19 hours
  5. temperatureOn cooling the reaction mixture
  6. extractionextracted with aqueous sodium hydroxide (5%) solution (2×5 mL)
  7. extractionextracted with chloroform (3×4 mL)
  8. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  9. customRemoval of solvent
  10. customon rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-3b8aca4417cf4ada848e3468cba3041f
Quelldatensatz
uspto-grants-1996_02
Patentnummer
US05492964

Verknüpfte Notizen

Wird geladen…