Sodium Hydroxide → 2-(4-acetylphenoxy)propanoic Acid

HRID 1165345ノート

反応式

HRID 1165345 の反応式
[C:1]([C:4]1[CH:16]=[CH:15][C:7]([O:8][CH:9]([CH3:14])[C:10]([O:12]C)=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH-].[Na+]>O>[C:1]([C:4]1[CH:16]=[CH:15][C:7]([O:8][CH:9]([CH3:14])[C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 14717334Methyl 2-(4-acetylphenoxy)propanoate

生成物 1

HCID 51606492-(4-acetylphenoxy)propanoic Acid収率 92%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a solution of the potassium salt of 4-hydroxyacetophenone (8.8 g, 0.05 mol) in dimethylformamide (25 mL) is added methyl 2-bromopropanoate (10.2 g, 0.06 mol) over 30 minutes and stirred at 80°-90° C. for 4 hours under nitrogen. The reaction is cooled to room temperature and methylene chloride (75 mL) and water (75 mL) are added. The organic phase is separated, washed with water (100 mL), dried and concentrated to give methyl 2-(4-acetylphenoxy)propanoate (8.5 g) (yield 76%). Methyl 2-(4-acetylphenoxy)propanoate (7.0 g, 31.5 mmol) is combined with 2N NaOH (20 mL) and refluxed overnight. Water (30 mL) is added to the reaction which is then washed with methylene chloride (50 mL). It is then acidified to pH=1 with concentrated hydrochloric acid and extracted with ethyl acetate (3×100 mL). The organic phase is dried and concentrated to provide 2-(4 -acetylphenoxy)propanoic acid (5.0 g) (yield 92%): m.p. 104.3° C., IR (KBr) 3000 (br, vs), 2940 (br,s), 1754 (vs), 1650 (vs); 1H NMR (CDCl3) delta 1.69 (d, J=6.8 Hz, 3H), 2.55 (s,3H), 4.8 (q, J=6.8 Hz, 1H), 6.92 and 7.93 (dd, J=9.0 Hz, 4H).

後処理

  1. temperaturerefluxed overnight
  2. washis then washed with methylene chloride (50 mL)
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. customThe organic phase is dried
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-1a030ba575c54bd2907b718a20de92de
出典データセット
uspto-grants-1990_03
特許番号
US04908476

反応ノート

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