Quinoline → 5-(2-Formyl-3-hydroxyphenoxy)pentanoic acid

HRID 647905

Reaction equation

HRID 647905 reaction equation
[CH:1]([C:3]1[C:16]([OH:17])=[C:15](C(O)=O)[CH:14]=[CH:13][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:2].N1C2C(=CC=CC=2)C=CC=1>[Cu]>[CH:1]([C:3]1[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:2]

Participants

4

Reactant 2

HCID 7047QuinolineHCID 204843435-(2-Formyl-3-hydroxy-4-carboxyphenoxy)pentanoic acid

Product 1

HCID 721625-(2-Formyl-3-hydroxyphenoxy)pentanoic acid

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

5-(2-Formyl-3-hydroxy-4-carboxyphenoxy)pentanoic acid (Example 6) (0.2 g, 0.0007 M), copper (0.05 g) and quinoline (5 ml) were heated at 210° C. for 1/2 hour. The reaction mixture was cooled and filtered. Ether (20 ml) was added to the filtrate and the organic layer was washed with 2 N hydrochloric acid (3×20 ml), water (1×20 ml) and brine (1×20 ml), dried (magnesium sulphate) and the solvent removed in vacuo to give 5-(2-formyl-3-hydroxyphenoxy)pentanoic acid as a pale-yellow oil that solidified on standing and was homogeneous on thin layer chromatography (silicagel plates; chloroform:methanol, 10:1).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. additionEther (20 ml) was added to the filtrate
  4. washthe organic layer was washed with 2 N hydrochloric acid (3×20 ml), water (1×20 ml) and brine (1×20 ml)
  5. dry with materialdried (magnesium sulphate)
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-dcc1b7c5cd4447009d6126ea1a57ae95
Source dataset
uspto-grants-1983_10
Patent number
US04410537

Linked notes

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