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

HRID 610687노트

반응식

HRID 610687 반응식
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

참가 물질

3

반응물 1

HCID 18795066Ethyl 2-ethoxycarbonyl-9-phenoxynonanoate

생성물 1

HCID 158876389-Phenoxy-nonanoic acid수율 85.9%

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

반응 조건

온도
190 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-69620aa2cad0493483935a9071917837
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998642

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