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

HRID 8080

Reaction equation

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

Participants

Reactant 2

HCID 8500p-METHYLACETOPHENONE

HCID 11120Dimethyl oxalate

Product 1

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

Procedure

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.

Workup

customrecrystallization

Sources & evidence

ORD record: ord-d315ddcc6d8d4f5e8190cb9892565d27
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087630B2

Linked notes

Loading…