Potassium Carbonate → 4-(3-Formylphenoxy)butanoic acid

HRID 964427Notes

Reaction equation

HRID 964427 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[O:6][CH2:7][CH2:8][CH2:9][C:10]([O:12]CC)=[O:11])=[O:2].C(=O)([O-])[O-].[K+].[K+]>CO.O>[CH:1]([C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[O:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[O:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 10466631Ethyl 4-(3-formylphenoxy)butanoate

Product 1

HCID 164956824-(3-Formylphenoxy)butanoic acidYield 92.8%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of 385 mg (1.63 mmol) of 4-(3-formylphenoxy)butanoic acid, ethyl ester and 850 mg (6.15 mmol) of potassium carbonate is stirred in 6 mL of methanol/water (3:2) at room temperature for 8 hours. The solution is then concentrated in vacuo. The residue is dissolved in 10 mL of 0.1N sodium hydroxide solution and washed with 20 mL of ether. The aqueous layer is separated and acidified with sodium bisulfate and extracted with ethyl acetate. The organic layer is washed with saturated sodium chloride solution, then dried over magnesium sulfate. The mixture is then filtered and concentrated in vacuo to give 315 mg of 4-(3-formylphenoxy)butanoic acid as a white solid. The product is utilized in the next reaction without further purification. m.p. 62°-63°; the 1H NMR (300 MHz, CDCl3) is consistent with the desired product; IR (KBr) 3400, 3000, 1700, 1690, 1590 cm-1 ; MS (CI low res) m/e 209 (M+H), 191, 123.

Workup

  1. concentrationThe solution is then concentrated in vacuo
  2. dissolutionThe residue is dissolved in 10 mL of 0.1N sodium hydroxide solution
  3. washwashed with 20 mL of ether
  4. customThe aqueous layer is separated
  5. extractionextracted with ethyl acetate
  6. washThe organic layer is washed with saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationThe mixture is then filtered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-04df0967ff494a1181b35eddfc7ffaf8
Source dataset
uspto-grants-1998_06
Patent number
US05767285

Reaction notes

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