Sodium Hydroxide → 2-(4-Methoxy-2-nitrophenyl)acetic acid

HRID 1914690ノート

反応式

HRID 1914690 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9](C(OCC)=O)[C:10]([O:12]CC)=[O:11])=[C:5]([N+:20]([O-:22])=[O:21])[CH:4]=1.[OH-].[Na+]>CCO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[C:5]([N+:20]([O-:22])=[O:21])[CH:4]=1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 1811374Diethyl (4-methoxy-2-nitrophenyl)malonate

生成物 1

HCID 114131802-(4-Methoxy-2-nitrophenyl)acetic acid収率 114%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
90 °C

実験手順

A solution of diethyl (4-methoxy-2-nitrophenyl)malonate (1.1 g; 3.53 mmol; 1 eq) in a mixture of EtOH (25 mL) and sodium hydroxide (25 mL; 1 M; 25 mmol; 7.07 eq) is heated for 1 h at 90° C. The solvents are removed under reduced pressure and the orange-yellow powder is suspended in THF (20 mL). After cooling down to 0° C., 5M HCl (20 mL) is added. The reaction mixture is refluxed at 85° C. for 1 h. After cooling down to room temperature, the 2 phases are separated and the organic phase is dried over MgSO4. The aqueous phase is treated twice with EtOAc (50 mL) and the combined organic phases are dried over MgSO4 then concentrated to dryness to afford 850 mg (100%) of the title compound as a brown solid. 1H NMR (DMSO-d6) δ 8.20-8.10 (m, 1H), 7.45 (d, J=3.0 Hz, 1H), 7.05 (d, J=8.0 Hz, 1H), 6.95 (dd, J=8.0, 3.0 Hz, 1H), 3.78 (s, 2H), 3.67 (s, 3H). HPLC (max plot) 89%; Rt 2.54 min. LC/MS: (ES+): 229.0 (M+NH4+).

後処理

  1. customThe solvents are removed under reduced pressure
  2. temperatureAfter cooling down to 0° C.
  3. addition5M HCl (20 mL) is added
  4. temperatureThe reaction mixture is refluxed at 85° C. for 1 h
  5. temperatureAfter cooling down to room temperature
  6. customthe 2 phases are separated
  7. dry with materialthe organic phase is dried over MgSO4
  8. additionThe aqueous phase is treated twice with EtOAc (50 mL)
  9. dry with materialthe combined organic phases are dried over MgSO4
  10. concentrationthen concentrated to dryness

出典と根拠

ORDレコード
ord-3ce8120065ed40428688fe654cdc05ec
出典データセット
uspto-grants-2013_12
特許番号
US08614215B2

反応ノート

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