Acetic Acid → 2-(4-Acetamidophenoxy)propionic acid

HRID 2254345노트

반응식

HRID 2254345 반응식
C([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH:9]([CH3:13])[C:10]([OH:12])=[O:11])=[CH:6][CH:5]=1)(=O)C.S(O)(O)(=O)=O.[NH2:21]O.C(=O)([O-])[O-].[Na+].[Na+].[C:29]([OH:32])(=O)[CH3:30]>S(=O)(=O)(O)O.O>[C:29]([NH:21][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH:9]([CH3:13])[C:10]([OH:12])=[O:11])=[CH:14][CH:15]=1)(=[O:32])[CH3:30]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 159255Hydroxylamine, sulfate (1:1)HCID 51606492-(4-acetylphenoxy)propanoic Acid

생성물 1

HCID 167904892-(4-Acetamidophenoxy)propionic acid수율 95%

시약·촉매·용매 2

HCID 1118Sulfuric Acid촉매HCID 962Water용매

실험 절차

A solution of 2-(4-acetylphenoxy)propionic acid (1.5 g, 7.2 mmol), hydroxylamine sulfate (0.72 g, 4.4 mmol), and concentrated sulfuric acid (2 drops) in acetic acid (30 mL) is refluxed for 4.25 hours. The reaction is quenched with sodium carbonate (0.25 g, 2.4 mmol) and concentrated to give a residue. The reaction residue is dissolved in water (50 mL) and extracted with ethyl acetate (2×100 mL). The ethyl acetate extract is dried and concentrated to give 2-(4-acetamidophenoxy)propionic acid (1.53 g) (yield 95%): m.p. 170°-172° C.; IR (KBr) 3400 (vs), 2900 (s) 1730 (vs), 1630 (vs), and 1603 (vs); 1H NMR (DMSO-d6) delta 1.47 (d, J=6.8 Hz, 3H), 1.87 (s,3H), 2.06 (s,3H), 4.65 (q, J=6.8 Hz, 1H), 6.73 and 7.42 (dd, J=9.0 Hz, 4H).

후처리

  1. concentrationconcentrated
  2. customto give a residue
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. extractionThe ethyl acetate extract
  5. customis dried
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5e20147a912140a3916ef8715e9811bd
출처 데이터셋
uspto-grants-1993_08
특허 번호
US05235090

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