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

HRID 647904Notes

Reaction equation

HRID 647904 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].O.[OH-].[Na+]>O1CCOCC1>[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

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 204843435-(2-Formyl-3-hydroxy-4-carboxyphenoxy)pentanoic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5-(2-Formyl-3-hydroxy-4-carboxyphenoxy)pentanoic acid (0.2 g, 0.0007 M), acidic alumina (0.1 g), water (10 ml) and dioxane (3 ml) were left at reflux for 4 days. The reaction mixture was cooled, and made alkaline by the addition of sodium hydroxide. The reaction mixture was filtered and the filtrate acidified with concentrated hydrochloric acid. The resulting precipitate was filtered and washed with a little water, then dried in a desiccator over phosphorus pentoxide to give the title compound as a pale-yellow solid, homogeneous on thin layer chromatography.

Workup

  1. temperatureat reflux for 4 days
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe reaction mixture was filtered
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with a little water
  6. dry with materialdried in a desiccator over phosphorus pentoxide

Sources & evidence

ORD record
ord-83a0171f6a7a4a3a900cc9b5587a8149
Source dataset
uspto-grants-1983_10
Patent number
US04410537

Reaction notes

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