Hydrochloric Acid → 4-(2,5-Dimethylphenoxy)butanoic acid

HRID 341344

Reaction equation

HRID 341344 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[OH:9].Br[CH:11]([CH2:17][CH3:18])[C:12]([O:14]CC)=[O:13].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[OH-].[Na+].Cl>CN(C)C(=O)C.C(O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][CH2:18][CH2:17][CH2:11][C:12]([OH:14])=[O:13]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 72672,5-DimethylphenolHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 79039Butanoic acid, 2-bromo-, ethyl ester

Product 1

HCID 15684184-(2,5-Dimethylphenoxy)butanoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
75 °C

Procedure

2,5-Dimethylphenol (6.1 g, 0.05 mol) and ethyl bromobutyrate were dissolved in 60 ml of N,N-Dimethylacetamide (DMAC). Potassium carbonate (11 g) and potassium iodide 0.5 g (0.003 mol) were added to this solution. The mixture was stirred at 70-80° C. for 24 hours. The filtrate was added to distilled water (200 ml). An oily precipitate formed and was extracted with methylene chloride (100 ml). The organic layer was washed with 5% sodium carbonate (3×150 ml), dried over anhydrous sodium sulfate, and concentrated to give al oily residue. The oil was dissolved in ethanol (5 ml). The solution was mixed with 2N sodium hydroxide (30 ml). The mixture was stirred at 70-80° C. until the ester was hydrolyzed (determined by HPLC). The solution was acidified with 3N hydrochloride to pH 1 to form a precipitate. The precipitate was collected by filtration and dissolved in 4% sodium bicarbonate. Insoluble materials were removed by filtration. The filtrate was acidified to pH 1 to form a precipitate. The precipitate was collected by filtration and air-dried. 6.6 g of 4-(2,5-dimethylphenoxy) butyric acid was recovered. Melting point: 63-65° C. Combustion analysis: % C. 69.21 (calcuated), 69.04 (found); % H, 7.74 (calculated); 7.49 (found). 1H NMR Analysis (d6-DMSO). δ 6.98, d, 1H; 6.71, s, 1H; 6.62, d, 1H; 3.94, t, 2H; 2.40, t, 2H; 2.24, s, 3H; 2.09, s, 3H; 1.95, p, 2H.

Workup

  1. additionThe filtrate was added
  2. distillationto distilled water (200 ml)
  3. customAn oily precipitate formed
  4. extractionwas extracted with methylene chloride (100 ml)
  5. washThe organic layer was washed with 5% sodium carbonate (3×150 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customto give al oily residue
  9. customto form a precipitate
  10. filtrationThe precipitate was collected by filtration
  11. dissolutiondissolved in 4% sodium bicarbonate
  12. customInsoluble materials were removed by filtration
  13. customto form a precipitate
  14. filtrationThe precipitate was collected by filtration
  15. customair-dried
  16. custom6.6 g of 4-(2,5-dimethylphenoxy) butyric acid was recovered

Sources & evidence

ORD record
ord-c6745f66e4ee475fa1411532351c19bf
Source dataset
uspto-grants-2014_11
Patent number
US08895777B2

Linked notes

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