Potassium Carbonate → 4-(4-Acetyl-2,6-dimethoxyphenoxy)butanoic acid

HRID 964434Notes

Reaction equation

[C:1]([C:4]1[CH:18]=[C:17]([O:19][CH3:20])[C:7]([O:8][CH2:9][CH2:10][CH2:11][C:12]([O:14]CC)=[O:13])=[C:6]([O:21][CH3:22])[CH:5]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>>[C:1]([C:4]1[CH:18]=[C:17]([O:19][CH3:20])[C:7]([O:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[C:6]([O:21][CH3:22])[CH:5]=1)(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 11430Potassium Carbonate

HCID 867527824-(4-Acetyl-2,6-dimethoxyphenoxy)butanoic acid, ethyl ester

Product 1

HCID 544557414-(4-Acetyl-2,6-dimethoxyphenoxy)butanoic acidYield 88%

Procedure

Following the method of Preparation 3, 0.179 g (0.577 mmol) of 4-(4-acetyl-2,6-dimethoxyphenoxy)butanoic acid, ethyl ester is treated with potassium carbonate, producing an off-white solid. Recrystallization from ethyl acetate/hexane gives 4-(4-acetyl-2,6-dimethoxyphenoxy)butanoic acid as white crystals (0.14 g, 88%): m.p. 122°-24° C.; IR (KBr) 1735, 1660 cm-1 ; 1H-NMR (CDCl3) is consistent with the desired product; MS (FAB) m/e 283 (M+ +H). Analysis calculated. for C14H18O6 : C, 59.57; H, 6.43; O, 34.01. Found: C, 59.34; H, 6.40; O, 34.26.

Workup

customproducing an off-white solid
customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record: ord-47f3a9d13b154474917ce52eac713268
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05767285

Reaction notes

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