Lithium hydroxide, monohydrate → 4-(2,4-Dichlorophenoxy)butyric acid

HRID 1875311ノート

反応式

HRID 1875311 の反応式
[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([O:10]CC)=[O:9].O[Li].O>C1COCC1.O>[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9]

参加物

5

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 12375252Ethyl 4-(2,4-dichloro-phenoxy)butanoate

生成物 1

HCID 14894-(2,4-Dichlorophenoxy)butyric acid収率 74.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of ethyl 4-(2,4-dichlorophenoxy)-butyrate (57 g, crude from last step, about 0.2 mol) in THF (500 mL) and water (500 mL) was added LiOH.H2O (12.6 g, 0.3 mol), and the reaction mixture was stirred for 5 h at RT. The mixture was washed with Et2O (3×200 mL), and the aqueous layer was acidified by addition of HCl (20%) to pH ˜2. The mixture was extracted with EtOAc (3×400 mL), the combined organic extracts were washed with water and brine, dried over Na2SO4 and concentrated in vacuo to give the butyric acid (37 g, 74.3% from 2,4-dichlorophenol) as a white solid. 1H-NMR (CDCl3): δ 7.36 (d, 1H, J=8.8 Hz), 7.18 (dd, 1H, J1=8.8 Hz, J2=2.4 Hz), 6.84 (d, 1H, J=8.8 Hz), 4.07 t, 2H, J=7.2 Hz), 2.64 (t, 2H, J=7.2 Hz), 2.17 (p, 2H, J=6.4 Hz).

後処理

  1. washThe mixture was washed with Et2O (3×200 mL)
  2. additionthe aqueous layer was acidified by addition of HCl (20%) to pH ˜2
  3. extractionThe mixture was extracted with EtOAc (3×400 mL)
  4. washthe combined organic extracts were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-269b1d1323624eddb28e1e0f5f407973
出典データセット
uspto-grants-2012_11
特許番号
US08309543B2

反応ノート

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