p-METHYLACETOPHENONE → Methyl 4-(4-methylphenyl)-2,4-dioxobutanoate

HRID 8080

Reaktionsgleichung

Reaktionsgleichung von HRID 8080
CO[C:3](=[O:8])[C:4]([O:6][CH3:7])=[O:5].[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[CH:12][CH:11]=1>>[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH2:17][C:3](=[O:8])[C:4]([O:6][CH3:7])=[O:5])=[CH:12][CH:11]=1

Komponenten

3

Edukt 2

HCID 8500p-METHYLACETOPHENONEHCID 11120Dimethyl oxalate

Produkt 1

HCID 308119Methyl 4-(4-methylphenyl)-2,4-dioxobutanoateAusbeute 74 %

Versuchsvorschrift

The title compound was prepared from dimethyloxalate (47.24 g, 400 mmol) and 4′-methylacetophenone (26.84 g, 200 mmol) using the procedure for Example 1d. Work-up and recrystallization provided the title compound as white needles (32.6 g, 74% yield). Mp 82–84° C. 1H NMR (300 MHz, CDCl3) δ 15.36 (br.s, 1H), 7.92 (d, J=8.3 Hz, 2H), 7.32 (d, J=8.3 Hz, 2H), 7.08 (s, 1H), 3.96 (s, 3H), 2.46 (s, 3H). Mass spectrum (API-TIS) m/z 221 (MH+). Anal calcd. for C12H12O4: C, 65.45; H, 5.49. Found: C, 65.46; H, 5.53.

Aufarbeitung

  1. customrecrystallization

Quellen und Nachweise

ORD-Eintrag
ord-d315ddcc6d8d4f5e8190cb9892565d27
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087630B2

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