Ethyl 2-ethoxycarbonyl-9-phenoxynonanoate → 9-Phenoxy-nonanoic acid

HRID 610687ノート

反応式

HRID 610687 の反応式
C([O:3][C:4]([CH:6]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)C(OCC)=O)=[O:5])C>[OH-].[Na+]>[O:19]([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:6][C:4]([OH:5])=[O:3])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

3

反応物 1

HCID 18795066Ethyl 2-ethoxycarbonyl-9-phenoxynonanoate

生成物 1

HCID 158876389-Phenoxy-nonanoic acid収率 85.9%

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

反応条件

温度
190 °C

実験手順

A solution of ethyl 2-ethoxycarbonyl-9-phenoxynonanoate (1.84 g, 5.3 mmol) in 20% NaOH (20 mL) was refluxed for 10 h. The solution was acidified with HCl(pH=2) and extracted with ethyl acetate (3×50 mL). The organic phase was washed with water (2×30 mL), and brine (30 mL), and dried over Na2SO4. After removal of the solvent in vacuo, the residue was heated on an oil bath at 180-200° C. for 10 min. The crude product was distilled (Kugelrohr) followed by crystallization (hexane) to give the product (1.14 g, 85%), mp 66.5-67.5° C. (lit.3 68-69° C.). IR: 3450-2500, 1720 cm-1 ; 1H-NMR: 1.26-1.39 (m, 8H), 1.61 (q, 2H), 1.75 (q, 2H), 2.34 (t, 2H), 3.93 (t, 2H), 6.83-6.96 (m, 3H), 7.28 (t, 2H), 10.8 (bs, 1H).

後処理

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe organic phase was washed with water (2×30 mL), and brine (30 mL)
  3. dry with materialdried over Na2SO4
  4. customAfter removal of the solvent in vacuo
  5. distillationThe crude product was distilled (Kugelrohr)
  6. customfollowed by crystallization (hexane)

出典と根拠

ORDレコード
ord-69620aa2cad0493483935a9071917837
出典データセット
uspto-grants-1999_12
特許番号
US05998642

反応ノート

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