Methylparaben → Methyl 4-{[2-(dimethylamino)-2-oxoethyl]oxy}benzoate

HRID 1874666Notes

Reaction equation

HRID 1874666 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:19][C:20]([N:22]([CH3:24])[CH3:23])=[O:21]>CN(C=O)C>[CH3:23][N:22]([CH3:24])[C:20](=[O:21])[CH2:19][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 11430Potassium Carbonate2×HCID 758862-chloro-N,N-dimethylacetamide2×

Product 1

HCID 45792893Methyl 4-{[2-(dimethylamino)-2-oxoethyl]oxy}benzoateYield 68.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 4-hydroxybenzoate (Fluka) (1.52 g, 10 mmol) and potassium carbonate (1.38 g, 10 mmol) in DMF (10 mL) was treated with 2-chloro-N,N-dimethylacetamide (Merck) (1.03 ml, 10 mmol) and the mixture was stirred at RT overnight. The reaction mixture was worked up by partitioning between ethyl acetate and 2M hydrochloric acid, washing with HCl, brine, dried (MgSO4) and evaporating to dryness. The residue was dissolved in DMF (5 mL) and treated with potassium carbonate (1.38 g, 10 mmol) and 2-chloro-N,N-dimethylacetamide (Merck) (1.03 ml, 10 mmol). The mixture was stirred at RT over the weekend, and then worked up. Partitioned between ethyl acetate and 2M HCl and the organic solution was washed with HCl (X2), brine (X3), dried (MgSO4), and evaporated to give the title compound (1.62 g, 68%) as a white solid. LCMS (System A) RT=0.73 min, ES+ve m/z 238 (M+H)+.

Workup

  1. customby partitioning between ethyl acetate and 2M hydrochloric acid
  2. washwashing with HCl, brine
  3. dry with materialdried (MgSO4)
  4. customevaporating to dryness
  5. dissolutionThe residue was dissolved in DMF (5 mL)
  6. stirringThe mixture was stirred at RT over the weekend
  7. customPartitioned between ethyl acetate and 2M HCl
  8. washthe organic solution was washed with HCl (X2), brine (X3)
  9. dry with materialdried (MgSO4)
  10. customevaporated

Sources & evidence

ORD record
ord-b04181af892b4480bb12886a6abc2173
Source dataset
uspto-grants-2012_11
Patent number
US08304446B2

Reaction notes

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