6-Methoxy-3-(trichloromethyl)-2-benzofuran-1(3H)-one → Benzoic acid, 2-(2,2-dichloroethenyl)-5-methoxy-

HRID 2170125Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2170125
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]([C:13](Cl)([Cl:15])[Cl:14])[O:8][C:9]2=[O:12])=[CH:5][CH:4]=1>[Zn].C(O)(=O)C>[Cl:14][C:13]([Cl:15])=[CH:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:11][C:10]=1[C:9]([OH:12])=[O:8]

Komponenten

4

Edukt 1

HCID 1578786-Methoxy-3-(trichloromethyl)-2-benzofuran-1(3H)-one

Produkt 1

HCID 11543295Benzoic acid, 2-(2,2-dichloroethenyl)-5-methoxy-Ausbeute 64,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A 100 mL round-bottomed flask containing a stirring bar was charged with 6-methoxy-3-(trichloromethyl)isobenzofuran-1(3H)-one (3.09 g, 10.94 mmol) and glacial acetic acid (40.0 mL). Zinc dust (2.86 g, 43.76 mmol) was added in small portions over 30 min. to the stirred reaction mixture. The reaction was left stirring at room temperature for further 30 min. and then heated at reflux for 1 h. It was filtered hot over a pad of Celite and the filtrates were diluted with water. The precipitate formed was collected by filtration and recrystallised from EtOH/H2O to give 2-(2,2-dichlorovinyl)-5-methoxybenzoic acid as white needles (1.74 g, 64%). Spectral data for this compound were consistent with those in the literature. M.p. 164-166° C. (lit. m.p. 167-168° C.); 1H NMR (400 MHz, DMSO-d6): δ=13.31 (br. s, 1H), 7.51 (d, J=8.7 Hz, 1H), 7.47-7.39 (m, 2H), 7.21 (dd, J=8.7 Hz, J=2.2 Hz, 1H), 3.82 (s, 3H).

Aufarbeitung

  1. additionA 100 mL round-bottomed flask containing a stirring bar
  2. waitThe reaction was left
  3. temperatureheated
  4. temperatureat reflux for 1 h
  5. filtrationIt was filtered hot over a pad of Celite
  6. additionthe filtrates were diluted with water
  7. customThe precipitate formed
  8. filtrationwas collected by filtration
  9. customrecrystallised from EtOH/H2O

Quellen und Nachweise

ORD-Eintrag
ord-d13c5a19b7eb4571b1b17d25dacde0e4
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09050586B2

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