Potassium Iodide → 2,2-diethoxyethyl Benzoate

HRID 13677

Reaction equation

HRID 13677 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+].[I-].[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 4875Potassium IodideHCID 6228DimethylformamideHCID 121282-Chloro-1,1-diethoxyethaneHCID 23661960Potassium Benzoate

Product 1

HCID 118172582,2-diethoxyethyl BenzoateYield 84.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Chloroacetaldehyde diethyl acetal (2.00 g), potassium benzoate (1.91 g), potassium iodide (0.41 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 separated, was subjected to vacuum concentration and then to Kugelrohr distillation at 110-120° C. and at 1 mmHg and thereby yielded the target compound (2.41 g) in a yield of 77%.

Workup

  1. temperatureby refluxing
  2. filtrationAfter filtration
  3. customthe organic layer was separated
  4. concentrationwas subjected to vacuum concentration
  5. distillationto Kugelrohr distillation at 110-120° C.

Sources & evidence

ORD record
ord-b38bb05c9a654ded9acc8930760c2a49
Source dataset
uspto-grants-2010_06
Patent number
US07728152B2

Linked notes

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