Sodium Hydroxide → 2-Hydroxy-3-methyl-4-oxo-4-(3',4'-dichlorophenyl)butanoic acid

HRID 430720

反応式

HRID 430720 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10](=O)[CH3:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[OH2:13].[C:14]([OH:18])(=[O:17])[CH:15]=[O:16].[OH-].[Na+].C(Cl)Cl.CO>C(O)C.O.C(OCC)C.CCCCCC>[OH:16][CH:15]([CH:10]([CH3:11])[C:9](=[O:13])[C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[C:14]([OH:18])=[O:17]

参加物

8

反応物 4

HCID 14798Sodium HydroxideHCID 810603',4'-DichloropropiophenoneHCID 15620607Glyoxylic acid, monohydrateHCID 21226129Dichloromethane methanol

生成物 1

HCID 100391462-Hydroxy-3-methyl-4-oxo-4-(3',4'-dichlorophenyl)butanoic acid収率 27%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 21584099Diethylether hexane溶媒

反応条件

温度
0 °C

実験手順

To a solution of 1-(3,4-dichlorophenyl)propanone (5.8 g, 28.5 mmol)in 95% ethanol (100 mL) a solution of glyoxylic acid monohydrate (2.63 g, 28.5 mmol) in water (20 mL) was added at 0° C., followed by dropwise addition of a solution of sodium hydroxide (4.6 g, 0.114 mol). The temperature during the addition was maintained below +5° C. on cooling. The resulting reaction mixture was stirred at 0° C. over 3 hours, then allowed to warm to room temperature and stirred further 12 hours. The most of ethanol was then removed under reduced pressure (15° C.), the residue was diluted with water and the pH of the obtained suspension adjusted to 2 by addition of 37% HCl, on stirring and cooling at 0° C. The aqueous phase was extracted with ethyl acetate, and the collected organic extracts were washed with brine, dried and evaporated to provide the crude reaction product as a light yellow oil (4.4 g). Column chromatography (SiO2; CH2Cl2/MeOH 95:5) provided the pure titled compound (2.1 g, 27%), colorless solid (Ethyl ether/hexane) mp. 103-104° C.;

後処理

  1. additionThe temperature during the addition
  2. temperaturewas maintained below +5° C.
  3. temperatureon cooling
  4. customThe resulting reaction mixture
  5. temperatureto warm to room temperature
  6. stirringstirred further 12 hours
  7. customThe most of ethanol was then removed under reduced pressure (15° C.)
  8. additionthe residue was diluted with water
  9. additionthe pH of the obtained suspension adjusted to 2 by addition of 37% HCl
  10. stirringon stirring
  11. temperaturecooling at 0° C
  12. extractionThe aqueous phase was extracted with ethyl acetate
  13. washthe collected organic extracts were washed with brine
  14. customdried
  15. customevaporated
  16. customto provide the crude

出典と根拠

ORDレコード
ord-d14c65e9109f43f5ba3b2ca71822351a
出典データセット
uspto-grants-2001_11
特許番号
US06323240B1

関連ノート

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