Water → 3,4-Dipropoxybenzoic acid

HRID 710399Notes

Reaction equation

HRID 710399 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][C:16]=1[O:17][CH2:18][CH2:19][CH3:20])[C:8]([O:10]CCC)=[O:9])[CH2:2][CH3:3].[OH-].[K+].O>O1CCOCC1>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][C:16]=1[O:17][CH2:18][CH2:19][CH3:20])[C:8]([OH:10])=[O:9])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 66726576Propyl 3,4-dipropoxybenzoate

Product 1

HCID 24429763,4-Dipropoxybenzoic acidYield 94%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of the product of Step A (0.94 g; 3.35 mmol), KOH (0.56 g; 10 mmol), H2O (2 ml) and dioxane was stirred at reflux overnight. After evaporation of solvents under reduced pressure, the residue was dissolved on H2O (5 ml) and insoluble material was removed by filtration. The filtrate was acidified to pH˜3 with diluted HCl and the product was taken up by extraction with CH2Cl2 (3×15 ml). The combined organic phase was dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness to give the title compound (0.75 g; 94%) as creamy solid. 1H-NMR (CDCl3) 1.02-1.08 (m, 6H); 1.79-1.93 (m, 4H); 3.98-4.05 (m, 4H); 6.87 (d, 1H, J=8.5 Hz); 7.57 (d, 1H, J=2 Hz)); 7.7 (dd, 1H, J=2, 8.5 Hz).

Workup

  1. temperatureat reflux overnight
  2. customAfter evaporation of solvents under reduced pressure
  3. dissolutionthe residue was dissolved on H2O (5 ml) and insoluble material
  4. customwas removed by filtration
  5. extractionthe product was taken up by extraction with CH2Cl2 (3×15 ml)
  6. dry with materialThe combined organic phase was dried over anhydrous MgSO4
  7. filtrationfiltered
  8. customfiltrate evaporated to dryness

Sources & evidence

ORD record
ord-058ccb4e4d094a33aeaa3aba909bdd1a
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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