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

HRID 1639413ノート

反応式

HRID 1639413 の反応式
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]

参加物

7

反応物 4

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

生成物 1

HCID 167904892-(4-Acetamidophenoxy)propionic acid収率 95%

試薬・触媒・溶媒 2

HCID 1118Sulfuric Acid触媒HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-66d10c86d8304d8b80651ce8c0cc7eb6
出典データセット
uspto-grants-1989_11
特許番号
US04883901

反応ノート

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