Water → 2-(2-Phenylethoxy)ethanol

HRID 530518ノート

反応式

HRID 530518 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:15][CH2:16][C:17](O)=[O:18])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O.[OH-].[K+]>CCOCC>[CH2:7]([O:15][CH2:16][CH2:17][OH:18])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

6

反応物 4

HCID 962Water2 回HCID 14797Potassium HydroxideHCID 132089222-(2-Phenylethoxy)acetic acidHCID 21226445Aluminium lithium hydride

生成物 1

HCID 132089292-(2-Phenylethoxy)ethanol収率 68%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
0 °C

実験手順

Under nitrogen atmosphere, at 0° C., to a stirring mixture of LiAlH4 (0.93 g, 24.63 mmol) in dry Et2O (60 mL), 2-phenethyloxyacetic acid (1.1 g, 6.15 mmol) in dry Et2O (6 mL) was added dropwise. The mixture was left to react at rt for 4 h, then at 0° C. H2O (0.93 mL), 3.0 M KOH solution (0.93 mL) and H2O (3.12 mL) were very slowly added. The mixture was stirred at 0° C. for 1 h, filtered to remove the solid residue, and the organic phase dried over Na2SO4. The organic solution was again filtered and concentrated to dryness. The crude mixture was purified by column chromatography using a Teledyne ISCO apparatus, eluting with Cy:EtOAc (from 100:0 to 60:40) affording the title compound (0.69 g, 68%) as a colorless oil. 1H NMR (DMSO-d6): δ 2.81 (t, J=7.1 Hz, 2H), 3.40-3.44 (m, 2H), 3.45-3.51 (m, 2H), 3.60 (t, J=7.1 Hz, 2H), 4.55 (t, J=5.4 Hz, 1H), 7.15-7.30 (m, 5H).

後処理

  1. additionwas added dropwise
  2. waitThe mixture was left
  3. customto react at rt for 4 h
  4. customat 0° C
  5. filtrationfiltered
  6. customto remove the solid residue
  7. dry with materialthe organic phase dried over Na2SO4
  8. filtrationThe organic solution was again filtered
  9. concentrationconcentrated to dryness
  10. customThe crude mixture was purified by column chromatography
  11. washeluting with Cy

出典と根拠

ORDレコード
ord-539ce4dd420d4d3f87f9e9689d578dcd
出典データセット
uspto-grants-2016_05
特許番号
US09353075B2

反応ノート

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