Potassium Carbonate → 4-[4-(3-Oxobutyl)phenoxy]butanoic acid

HRID 964435Notes

Reaction equation

HRID 964435 reaction equation
[O:1]=[C:2]([CH3:20])[CH2:3][CH2:4][C:5]1[CH:19]=[CH:18][C:8]([O:9][CH2:10][CH2:11][CH2:12][C:13]([O:15]CC)=[O:14])=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+]>CO.O>[O:1]=[C:2]([CH3:20])[CH2:3][CH2:4][C:5]1[CH:19]=[CH:18][C:8]([O:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 23119605Ethyl 4-[4-(3-oxobutyl)phenoxy]butanoate

Product 1

HCID 246884044-[4-(3-Oxobutyl)phenoxy]butanoic acidYield 60%

Reagents, catalysts & solvents 1

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

Procedure

4-[4-(3-Oxobutyl)phenoxy]butanoic acid, ethyl ester (716 mg, 2.57 mmol) is dissolved in 5 mL of methanol/water (3:2) and treated with 1.24 g (9.0 mmol) of potassium carbonate according to the procedure described for Example 4 to give 385 mg (60%) of 4-[4-(3-oxobutyl)phenoxy]butanoic acid as a white powder: m.p. 97°-99°; the 1H NMR (300 MHz, CDCl3) is consistent with the desired product; IR (neat) 1730, 1700, 1620, 1520 cm-1 ; Analysis calculated for C14H18O4 : C, 67.18; H, 7.25; found: C, 66.55; H, 7.09.

Sources & evidence

ORD record
ord-9989c15b8264453d9a49f0d799ee8beb
Source dataset
uspto-grants-1998_06
Patent number
US05767285

Reaction notes

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