Hydrochloric Acid → methyl 4-(4-chlorophenyl)-2,4-dioxobutanoate

HRID 1356890Notes

Reaction equation

HRID 1356890 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[C:2]([O:4]C)=O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[CH:12][CH:11]=1.C[O-].[Na+].Cl>CO>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH2:17][C:2](=[O:4])[C:1]([O:7][CH3:8])=[O:6])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7467P-ChloroacetophenoneHCID 11120Dimethyl oxalateHCID 10942334Sodium Methoxide

Product 1

HCID 308124methyl 4-(4-chlorophenyl)-2,4-dioxobutanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dimethyl oxalate (15.27 g, 0.129 mol) and 4′-chloroacetophenone (20.0 g, 0.129 mol) were charged to a 500 mL round-bottom flask, with provisions made for magnetic stirring, and diluted with methanol (300 mL). Sodium methoxide (25% in methanol, 70 mL) was added in one portion. The reaction was stirred at room temperature for 16 hours. The reaction became an insoluble mass during this time. The solid was mechanically broken up, then concentrated hydrochloric acid (70 mL) was added, and the white suspension was stirred vigorously at room temperature for sixty minutes. The suspension was cooled to 0° C. and held for 30 minutes. The soild was filtered, and the filter cake was washed with cold water (100 mL). Upon drying, methyl 4-[4-(chloro)phenyl]-2,4-dioxobutanoate was obtained (16.94 g, 54.4%) as the enol: 1H NMR (CDCl3/300 MHz) 7.94 (d, J=8.66 Hz, 2H), 7.48 (d, J=8.66 Hz, 2H), 7.04 (s, 1H), 3.95 (s, 3H), 3.48 (s, 1H).

Workup

  1. stirringthe white suspension was stirred vigorously at room temperature for sixty minutes
  2. temperatureThe suspension was cooled to 0° C.
  3. waitheld for 30 minutes
  4. filtrationThe soild was filtered
  5. washthe filter cake was washed with cold water (100 mL)
  6. customUpon drying

Sources & evidence

ORD record
ord-22565fc186064439b8f795139d3713a9
Source dataset
uspto-grants-2003_07
Patent number
US06586603B1

Reaction notes

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