Dimethyl Sulfone → Methyl 3-phenylpropionate

HRID 1378901Notes

Reaction equation

HRID 1378901 reaction equation
CS(C)(=O)=[O:3].[H-].[Na+].Br[C:9]1[CH:14]=[CH:13][C:12](OC(OC)C)=[CH:11][CH:10]=1.[O:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>CS(C)=O>[C:9]1([CH2:23][CH2:22][C:21]([O:20][CH3:24])=[O:3])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 6213Dimethyl SulfoneHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 22908633p-Bromo-(1-methoxyethoxy)benzene

Product 1

HCID 7643Methyl 3-phenylpropionate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of dimethylsulfone (42 g, 0.45 mole) in dimethylsulfoxide (225 ml), 60% sodium hydride (17.9 g, 0.45 mole) was added in a small portion at 18°-20° C., stirring was continued at 65°-70° C. for 30 minutes, and then diluted with tetrahydrofuran (225 ml). Then to this mixture, a solution of methyl 3-phenylpropionate (36.6 g, 0.22 mole) obtained in above (1) in tetrahydro-furan (110 ml) was added dropwise at 33°-41° C., and reacted with stirring for 1 hour. After cooling, the reaction mixture was poured into diluted hydrochloric acid, and extracted 5 times with chloroform (100 ml). The organic layer was washed thrice with H2O (200 ml), saturated aqueous sodium bicarbonate (200 ml), then H2O (200 ml), dried over anhydrous MgSO4 and evaporated. The crude solid (60.8 g) was recrystallized from ethyl acetate to afford 24.7 g of 1-methylsulfonyl-4-phenylbutan-2-one as white needles having a melting point of 97.6-°98.4° C.

Sources & evidence

ORD record
ord-7803eec2ee6e4c1886e862231d8d19e3
Source dataset
uspto-grants-1997_09
Patent number
US05670299

Reaction notes

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