Hydrochloric Acid → Methyl (4-chlorobenzoyl)acetate

HRID 1607211Notes

Reaction equation

HRID 1607211 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 additional 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. NMR data was consistent with the structure.

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-0c209d425db24dc7917fddd9502a67b4
Source dataset
uspto-grants-1989_09
Patent number
US04863947

Reaction notes

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