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

HRID 257722

Reaktionsgleichung

Reaktionsgleichung von HRID 257722
[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 954,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7044DecalinLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a suspension of 2-methyl-1,4-dihydrobenzoic acid (0.085 g, 0.05 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). The solution was heated to reflux for 19 h. 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) δ8..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, 1H), 7.22 (dd, J=8.5, 1.5 Hz, 1H), 2.64 (s, 3H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-f43c679603694864b00aac60e59cd5bb
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05264408

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