Methylparaben → HCID 23109554, compound

HRID 968972Notes

Reaction equation

HRID 968972 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].[OH:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:20][CH:21]=1)(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 96744o-Fluoroacetophenone

Product 1

HCID 23109554HCID 23109554, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
140 °C

Procedure

2′-Fluoroacetophenone (10.6 g), methyl 4-hydroxybenzoate (11.7 g) and potassium carbonate (11.2 g) were suspended in dimethylacetamide (70 ml), and the mixture was stirred at 140° C. for one day. The reaction mixture was cooled to room temperature and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=7:1) to give the title compound (8.62 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=7:1)

Sources & evidence

ORD record
ord-b0e328c7de744bf48a2aebb90db1bf24
Source dataset
uspto-grants-2007_12
Patent number
US07304174B2

Reaction notes

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