Hydrochloric Acid → Methyl 3-(3,4-dimethylphenyl)-3-oxopropanoate

HRID 1785418Notes

Reaction equation

HRID 1785418 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:10])=[O:9])=[CH:4][C:3]=1[CH3:11].[K].[CH3:13][O:14][C:15](=O)[O:16]C.Cl>O1CCCC1>[CH3:13][O:14][C:15](=[O:16])[CH2:10][C:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([CH3:11])[CH:4]=1)=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 12021Dimethyl CarbonateHCID 771933,4-DimethylacetophenoneHCID 5462222Potassium

Product 1

HCID 2758622Methyl 3-(3,4-dimethylphenyl)-3-oxopropanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 3,4-dimethylacetophenone (1.0 g, 6.8 mmol) in tetrahydrofuran (10 ML) at 0° C. under an atmosphere of nitrogen was added potassium hexamethyldisilylzide (1.46 g, 6.8 mmol). Resulting suspension was stirred for 10 min and dimethylcarbonate (0.58 mL, 6.8 mmol) added. Reaction stirred for 16 h warming to room temperature then poured onto wet ice (50 mL)/ hydrochloric acid (5 mL). Product extracted with ethyl acetate (50 mL) and organic washed with saturated sodium chloride then dried over magnesium sulfate. Product isolated as an amber oil after removal of solvent under vacuum. M+1=207.

Workup

  1. customResulting suspension
  2. customReaction
  3. stirringstirred for 16 h
  4. extractionProduct extracted with ethyl acetate (50 mL)
  5. washorganic washed with saturated sodium chloride
  6. dry with materialthen dried over magnesium sulfate
  7. customProduct isolated as an amber oil
  8. customafter removal of solvent under vacuum

Sources & evidence

ORD record
ord-2f44bf38eb3745459274ac3dbbeecdfa
Source dataset
uspto-grants-2009_03
Patent number
US07504403B2

Reaction notes

Loading…