Hydrochloric Acid → Methyl (4-chlorobenzoyl)acetate

HRID 978162Notes

Reaction equation

HRID 978162 reaction equation
[H-].[Na+].[C:3](=[O:8])([O:6][CH3:7])OC.[CH3:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[O:11].[H][H].Cl>O1CCCC1>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:10](=[O:11])[CH2:9][C:3]([O:6][CH3:7])=[O:8])=[CH:13][CH:14]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7467P-ChloroacetophenoneHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 735885Methyl (4-chlorobenzoyl)acetateYield 58.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 1000 ml three necked flask equipped with an addition funnel, and condenser was added 15.4 g of 60% sodium hydride (0.63 mole). The sodium hydride was washed twice with hexane and then suspended in 300 ml of tetrahydrofuran and 29 g of dimethyl carbonate (0.32 mole). The reaction mixture was brought to reflux and a solution of 50 g (0.32 mole) of 4-chloroacetophenone in 50 ml of tetrahydrofuran was added over 30 minutes. After hydrogen evolution had ceased the reaction was cooled and poured onto ice. The aqueous layer was acidified with hydrochloric acid and extracted with ethyl ether. The organic layer was dried, concentrated, and distilled at 15 torr bp 180°-205° C. to give 40 g of methyl 3-(4-chlorophenyl)-3-keto-propanoate.

Workup

  1. washThe sodium hydride was washed twice with hexane
  2. temperatureto reflux
  3. temperaturewas cooled
  4. additionpoured onto ice
  5. extractionextracted with ethyl ether
  6. customThe organic layer was dried
  7. concentrationconcentrated
  8. distillationdistilled at 15 torr bp 180°-205° C.

Sources & evidence

ORD record
ord-4f55e4b29a994af3941c4e8c3ee6a6c4
Source dataset
uspto-grants-1987_05
Patent number
US04663341

Reaction notes

Loading…