Potassium Carbonate → 3-(4-propoxyphenyl)propanoic acid

HRID 858586Notes

Reaction equation

O[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([O:12]C)=[O:11].I[CH2:15][CH2:16][CH3:17].C([O-])([O-])=[O:19].[K+].[K+]>CN(C=O)C>[CH2:15]([O:19][C:6]1[CH:7]=[CH:2][C:3]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:4][CH:5]=1)[CH2:16][CH3:17]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl 3-(hydroxyphenyl)propionate (15 g, 83.24 mmol) and iodopropane (12.14 mL, 124.5 mmol) in DMF (80 mL) was added K2CO3 (34 g, 249.7 mmol). The resultant slurry was stirred vigorously and heated to 60° C. under argon for 12 h. DMF was evaporated and residue partitioned between EtOAC and 1N HCl. The organic layer was washed with H2O, and brine then dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by flash column chromatography (10% EtOAc in hexanes) to provide the desired product (17 g, 98%) as a clear oil. The resultat oil was dissolved in THF (150 mL), and 2M NaOH (68 mL) was added. The reaction was stirred overnight at room temperature. THF was evaporated and residue acidified with concentrated HCl and extracted 3 times with EtOAC, (100 mL). The organic layer was washed with H2O, dried over Na2SO4 and concentrated to a white solid which was recrystalized from hexanes to provide the desired product (14.06 g 82%).

Workup

customDMF was evaporated
customresidue partitioned between EtOAC and 1N HCl
washThe organic layer was washed with H2O, and brine
dry with materialthen dried over Na2SO4
customThe solvent was removed in vacuo
customthe residue was purified by flash column chromatography (10% EtOAc in hexanes)

Sources & evidence

ORD record: ord-f570dba210964d789c8431bb48670f5d
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148226B2

Reaction notes

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