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

HRID 2254344노트

반응식

HRID 2254344 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 51606492-(4-acetylphenoxy)propanoic Acid수율 92%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7e0af63fb79a48859adfb352495ee532
출처 데이터셋
uspto-grants-1993_08
특허 번호
US05235090

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