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

HRID 962966Notes

Reaction equation

HRID 962966 reaction equation
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

Participants

3

Reactant 1

HCID 18795066Ethyl 2-ethoxycarbonyl-9-phenoxynonanoate

Product 1

HCID 158876389-Phenoxy-nonanoic acidYield 85.9%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

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: 3450-2550, 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).

Workup

  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. temperaturethe residue was heated on an oil bath at 180°-200° C. for 10 min
  6. distillationThe crude product was distilled (Kugelrohr)
  7. customfollowed by crystallization (hexane)

Sources & evidence

ORD record
ord-9255257bb7b94d85835307d8d4fc48ee
Source dataset
uspto-grants-1998_06
Patent number
US05760259

Reaction notes

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