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

HRID 610687Notes

Reaction equation

HRID 610687 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

Conditions

Temperature
190 °C

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: 3450-2500, 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).

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. distillationThe crude product was distilled (Kugelrohr)
  6. customfollowed by crystallization (hexane)

Sources & evidence

ORD record
ord-69620aa2cad0493483935a9071917837
Source dataset
uspto-grants-1999_12
Patent number
US05998642

Reaction notes

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