Methylparaben → Methyl 4-(difluoromethoxy)benzoate

HRID 1695242Notes

Reaction equation

HRID 1695242 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Cl[C:13]([F:18])([F:17])C([O-])=O.[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:13]([F:18])[F:17])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 2734985Sodium chlorodifluoroacetate

Product 1

HCID 7017143Methyl 4-(difluoromethoxy)benzoateYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

Under N2 flow, 1.3 g of 4-hydroxy-benzoic acid methyl ester (8.3 mmol, 1.0 eq) and 1.5 g of sodium chlorodifluoroacetate (10.0 mmol, 1.2 eq) were dissolved in DMF (25 mL) in a two neck round bottom flask; potassium carbonate (1.4 g, 10.0 mmol, 1.2 eq) was added and the mixture was heated at 125° C. for 3.5 hours. The mixture was then diluted with water and extracted with DCM; organic phases were dried and evaporated, the crude was purified with Si column (eluent: cycloexane/EtOAc 80/20) to obtain 0.77 g of product (yield 46%) which was used directly for the next step.

Workup

  1. extractionextracted with DCM
  2. customorganic phases were dried
  3. customevaporated
  4. customthe crude was purified with Si column (eluent: cycloexane/EtOAc 80/20)

Sources & evidence

ORD record
ord-84f5b03aa6a74394b4a48ff6688ee11b
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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