Potassium Carbonate → 4-(4-formyl-2-methoxyphenoxy)butanoic acid

HRID 964878Notes

Reaction equation

HRID 964878 reaction equation
[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][CH2:8][CH2:9][CH2:10][C:11]([O:13]CC)=[O:12])=[C:5]([O:18][CH3:19])[CH:4]=1)=[O:2].C(=O)([O-])[O-].[K+].[K+]>CO.O>[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[C:5]([O:18][CH3:19])[CH:4]=1)=[O:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 2736729ethyl 4-(4-formyl-2-methoxyphenoxy)butanoate

Product 1

HCID 17144474-(4-formyl-2-methoxyphenoxy)butanoic acidYield 58.3%

Reagents, catalysts & solvents 1

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

Procedure

4-(4-Formyl-2-methoxyphenoxy)butanoic acid, ethyl ester (240 mg, 0.90 mmol) is dissolved in 3 mL of methanol/water (3:2) and treated with 435 mg (3.15 mmol) of potassium carbonate according to the procedure described for Example 4 to give 125 mg (58%) of 4-(4-formyl-2-methoxyphenoxy)butanoic acid as a white powder: m.p. 143°-148°; the 1H NMR (300 MHz, CDCl3) is consistent with the desired product; IR (KBr) 3575, 3500, 1720, 1700, 1680, 1600, 1585 cm-1 ; MS (CI (low res)) m/e 239 (M+H), 221, 207, 153.

Sources & evidence

ORD record
ord-4025ff11b08146b1b84d21fcf80622f4
Source dataset
uspto-grants-1998_06
Patent number
US05773001

Reaction notes

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