P-Chloroacetophenone → Methyl 3-oxo-4-(4-chlorophenyl)butanoate

HRID 263644

反応式

HRID 263644 の反応式
[C:1]([O:7][CH3:8])(=[O:6])[C:2](OC)=O.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=O)[CH3:17])=[CH:12][CH:11]=1.C[O-].[Na+].[Na].C([O-])(=[O:27])CCC>CO>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17](=[O:27])[CH2:2][C:1]([O:7][CH3:8])=[O:6])=[CH:12][CH:11]=1

参加物

7

反応物 5

HCID 7467P-ChloroacetophenoneHCID 11120Dimethyl oxalateHCID 104775ButyrateHCID 5360545SodiumHCID 10942334Sodium Methoxide

生成物 1

HCID 22246215Methyl 3-oxo-4-(4-chlorophenyl)butanoate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Dimethyl oxalate (15.27 g, 0,129 mol), and 4'-chloroacetophenone (20.0 g, 0.129 mol) were added to methanol (300 mL). Sodium methoxide (25 wt. % in methanol, 70 mL) was added dropwise over about 0.5 hour. The reaction was stirred at room temperature for 16 hours, whereupon the sodium salt of the butanoate precipitated from solution. The mixture was treated with 70 mL of conc. HCl and the white suspension was stirred vigorously at room temperature for 1 hour. The suspension was cooled to 0° C. and held for 0.5 hour. The solid was filtered, and the filter cake was washed with cold water (100 mL). After drying in vacuo, methyl 4-[4-(chloro)phenyl]-3-ketobutyrate was obtained (16.94 g, 54.4%) as the enol: 1H NMR (CDCl3 /300 MHz) 8 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).

後処理

  1. customprecipitated from solution
  2. additionThe mixture was treated with 70 mL of conc. HCl
  3. temperatureThe suspension was cooled to 0° C.
  4. waitheld for 0.5 hour
  5. filtrationThe solid was filtered
  6. washthe filter cake was washed with cold water (100 mL)
  7. customAfter drying in vacuo

出典と根拠

ORDレコード
ord-fc6349c0750e4c6fae39c6f3f62f6318
出典データセット
uspto-grants-1997_07
特許番号
US05643933

関連ノート

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