Dimethylformamide → 2,2-diethoxyethyl Benzoate

HRID 640745Notes

Reaction equation

HRID 640745 reaction equation
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5]Cl)[CH3:2].[C:10]([O-:18])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[K+].[Br-].[K+].CN(C=O)C>C(OCC)(=O)C.O>[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5][O:18][C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:2]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 121282-Chloro-1,1-diethoxyethaneHCID 253877Potassium BromideHCID 23661960Potassium Benzoate

Product 1

HCID 118172582,2-diethoxyethyl BenzoateYield 34.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Chloroacetaldehyde diethyl acetal (2.00 g), potassium benzoate (1.91 g), potassium bromide (0.30 g) and DMF (20 mL) were placed in a three-neck flask, followed by refluxing. Twenty hours later, the reaction mixture was cooled to room temperature, and water (30 mL) and ethyl acetate (80 mL) were added thereto, followed by stirring. After filtration, the organic layer was washed with water (30 mL) and was dried over anhydrous sodium sulfate. Subsequent filtration and vacuum concentration yielded the target compound (0.97 g) in a yield of 31%.

Workup

  1. temperatureby refluxing
  2. filtrationAfter filtration
  3. washthe organic layer was washed with water (30 mL)
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationSubsequent filtration and vacuum concentration

Sources & evidence

ORD record
ord-d69dc31bd9f3447b8c48e1dabbfa7fea
Source dataset
uspto-grants-2010_04
Patent number
US07692033B2

Reaction notes

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