Sodium Hydroxide → 2-(3-(Cyclopropylmethoxy)-4-nitrophenyl)acetic acid

HRID 1183665ノート

反応式

HRID 1183665 の反応式
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:15](C(OCC)=O)[C:16]([O:18]CC)=[O:17])[CH:9]=[CH:10][C:11]=2[N+:12]([O-:14])=[O:13])[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH2:15][C:16]([OH:18])=[O:17])[CH:9]=[CH:10][C:11]=2[N+:12]([O-:14])=[O:13])[CH2:2][CH2:3]1

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 57995590Diethyl 2-(3-(cyclopropylmethoxy)-4-nitrophenyl)malonate

生成物 1

HCID 579955402-(3-(Cyclopropylmethoxy)-4-nitrophenyl)acetic acid収率 90.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

Compound diethyl 2-(3-(cyclopropylmethoxy)-4-nitrophenyl)malonate (10 g) was dissolved in 100 mL ethanol and cooled to 0° C., NaOH solution (4 eq) was added slowly to the reaction mixture for about 15 min. The reaction mixture was heated gently up to 60° C. for 5 h. Progress of the reaction was monitored by TLC analysis. After complete conversion of starting material solvent was evaporated under reduced pressure, residue dissolved in H2O, acidified with 6N HCl to pH-2. Filtered the solid material washed with water, dried under reduced pressure to give 2-(3-(cyclopropylmethoxy)-4-nitrophenyl)acetic acid (6.5 g) as a yellow solid. 1H-NMR (CDCl3, 200 MHz): 0.36 (m, 2H), 0.58 (m, 2H), 1.28 (m, 1H), 3.71 (s, 2H), 4.01 (d, 2H), 7.02 (d, 1H), 7.23 (s, 1H), 7.81 (d, 1H).

後処理

  1. temperatureThe reaction mixture was heated gently up to 60° C. for 5 h
  2. customAfter complete conversion of starting material solvent was evaporated under reduced pressure, residue
  3. dissolutiondissolved in H2O
  4. filtrationFiltered the solid material
  5. washwashed with water
  6. customdried under reduced pressure

出典と根拠

ORDレコード
ord-cfa1ad7be7f24ff2b36091719152dfe6
出典データセット
uspto-grants-2014_03
特許番号
US08664249B2

反応ノート

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