Acetic Acid → 2-{p-[(3,5-Dichloro-2-pyridyl)oxy]phenoxy}propionaldehyde

HRID 1108944ノート

反応式

HRID 1108944 の反応式
[Cl:1][C:2]1[C:3]([O:9][C:10]2[CH:23]=[CH:22][C:13]([O:14][CH:15]([CH3:21])[C:16](OCC)=[O:17])=[CH:12][CH:11]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.[H-].C([Al+]CC(C)C)C(C)C.C(O)(=O)C.CCCCCCC>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([O:9][C:10]2[CH:23]=[CH:22][C:13]([O:14][CH:15]([CH3:21])[CH:16]=[O:17])=[CH:12][CH:11]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 8900HeptaneHCID 2829855Propanoic acid, 2-[4-[(3,5-dichloro-2-pyridinyl)oxy]phenoxy]-, ethyl esterHCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 157666762-{p-[(3,5-Dichloro-2-pyridyl)oxy]phenoxy}propionaldehyde収率 91.5%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
-55 °C

実験手順

A solution of ethyl 2-{p-[(3,5-dichloro-2-pyridyl)oxy]phenoxy}propionate (1,455 g, 4.06 mol) in toluene (12 L) is cooled to -55° C. under a nitrogen atmosphere and diisobutylaluminum hydride (5.42 L of a 1.0M solution) is added over 2 hours. The reaction mixture is then stirred for 5 hours at -55° C. and glacial acetic acid (1.8 L) is added dropwise, while allowing the mixture to exotherm to 15° C. Heptane (12 L) is added and the mixture is washed sequentially with 5% hydrochloric acid solution, water, saturated sodium bicarbonate solution and water and concentrated in vacuo to obtain the title product as a yellow-orange liquid (1,159 g) which is identified by 1HNMR spectral analysis.

後処理

  1. customto exotherm to 15° C
  2. washthe mixture is washed sequentially with 5% hydrochloric acid solution, water, saturated sodium bicarbonate solution and water
  3. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a0980841fa5540b58c2e9ba487f94d8a
出典データセット
uspto-grants-1994_06
特許番号
US05318946

反応ノート

読み込み中…