Ethanol → 3-(4-Benzyloxy-2-nitrophenyl)-2-oxopropanoic acid

HRID 987263

反応式

HRID 987263 の反応式
[O-]CC.[K+].C(O)C.[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([N+:23]([O-:25])=[O:24])[CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:26](OCC)(=[O:32])[C:27]([O:29]CC)=[O:28]>C1(C)C=CC=CC=1.C(OCC)C>[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:26](=[O:32])[C:27]([OH:29])=[O:28])=[C:18]([N+:23]([O-:25])=[O:24])[CH:17]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

参加物

7

反応物 4

HCID 702EthanolHCID 7268Diethyl OxalateHCID 28015074-Benzyloxy-2-nitrotolueneHCID 23670592Potassium ethoxide

生成物 1

HCID 229886813-(4-Benzyloxy-2-nitrophenyl)-2-oxopropanoic acid収率 89.8%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

Potassium ethoxide (505 g; 6 mole) was added to a solution of ethanol (710 ml) and diethyl ether (4.8 l) and the mixture was cooled to 0° C. 4-(Benzyloxy)-1-methyl-2-nitrobenzene (639.8 g; 3 mole) dissolved in diethyl oxalate (900 g; 6.16 mole) and toluene (1500 ml) was added slowly during 30 minutes. The reaction mixture was stirred for 3 hours at 0° C. and then allowed to stand cold over night. After 5 days at room temperature the reaction mixture was filtered and the filter cake was washed with diethyl ether (2 l). The cake was then treated with water (10 l), sodium hydroxide (5 M, 0.8 l) and extracted three times with diethyl ether (3×3 l). The water phase was cooled and acidified in two steps while stirring with hydrochloric acid:water (1:1, 0.9 l). First to pH 5 and the reaction mixture was then stirred for 1 hour before the acidification continued to pH 2. The reaction mixture was cooled in an ice:sodium chloride bath. Filtration after 1 hour gave 849.5 g (89.8%) of 3-(4-benzyloxy-2-nitrophenyl)-2-oxopropanoic acid.

後処理

  1. waitto stand cold over night
  2. filtrationAfter 5 days at room temperature the reaction mixture was filtered
  3. washthe filter cake was washed with diethyl ether (2 l)
  4. additionThe cake was then treated with water (10 l), sodium hydroxide (5 M, 0.8 l)
  5. extractionextracted three times with diethyl ether (3×3 l)
  6. temperatureThe water phase was cooled
  7. stirringwhile stirring with hydrochloric acid:water (1:1, 0.9 l)
  8. stirringFirst to pH 5 and the reaction mixture was then stirred for 1 hour before the acidification
  9. temperatureThe reaction mixture was cooled in an ice
  10. filtrationFiltration after 1 hour

出典と根拠

ORDレコード
ord-af73158930884f219dc43e1d3840def5
出典データセット
uspto-grants-2003_10
特許番号
US06630600B1

関連ノート

読み込み中…