Potassium Carbonate → Ibuprofen, (+-)-

HRID 1198006Notes

Reaction equation

C(C1C=CC(CC(OC)=O)=CC=1)C(C)C.C(=O)(OC)OC.C([O-])([O-])=O.[K+].[K+].[CH2:28]([C:32]1[CH:37]=[CH:36][C:35]([CH:38]([CH3:43])[C:39]([O:41]C)=[O:40])=[CH:34][CH:33]=1)[CH:29]([CH3:31])[CH3:30]>>[OH:41][C:39]([CH:38]([C:35]1[CH:34]=[CH:33][C:32]([CH2:28][CH:29]([CH3:30])[CH3:31])=[CH:37][CH:36]=1)[CH3:43])=[O:40]

Participants

Reactant 4

HCID 11430Potassium Carbonate

HCID 12021Dimethyl Carbonate

HCID 109101Ibuprofen methyl ester

HCID 10987436Methyl 2-(4-isobutylphenyl)acetate

Product 1

HCID 3672Ibuprofen, (+-)-

Procedure

Following the procedure of example 1, a mixture of 2 g of methyl (4-isobutylphenyl)acetate (EP 347,939), 16 ml of dimethyl carbonate and 2 g of K2CO3, in a 1:20:1.5 molar ratio, is reacted in autoclave at a temperature of 210° C. The reaction is completed within about 8 hours. The product, methyl α-(4-isobutylphenyl)propionate, is hydrolyzed to α-(4-isobutyl)propionic acid (Ibuprofen) as in the examples above. Yield (starting from the not methylated ester): 90%.

Workup

customin a 1:20:1.5 molar ratio, is reacted in autoclave at a temperature of 210° C
customYield (

Sources & evidence

ORD record: ord-e25ddc6a78dd4955ae9d45dc3c56f934
Source dataset: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05278333

Reaction notes

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