Potassium Iodide → 2-Benzoyloxy-1,1-dimethoxy-ethane

HRID 13676Notes

Reaction equation

HRID 13676 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4]Cl.[C:8]([O-:16])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[K+].[I-].[K+].CN(C)C=O>C(OCC)(=O)C.O>[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][O:16][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 609862-Chloro-1,1-dimethoxyethaneHCID 23661960Potassium Benzoate

Product 1

HCID 116081762-Benzoyloxy-1,1-dimethoxy-ethaneYield 72.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Chloroacetaldehyde dimethyl acetal (50.0 g), potassium benzoate (70.7 g), potassium iodide (6.66 g) and DMF (N,N-dimethylformamide) (250 mL) were placed in a three-neck flask, followed by refluxing. Twenty hours later, the reaction mixture was cooled to room temperature, and water (250 mL) and ethyl acetate (250 mL) were added thereto, followed by stirring. After filtration, the filtrate was extracted with ethyl acetate (500 mL). The organic layer was subjected to vacuum concentration and then to vacuum distillation at 132-135° C. and at 5 mmHg and thereby yielded the target compound (61.0 g) in a yield of 72%.

Workup

  1. temperatureby refluxing
  2. filtrationAfter filtration
  3. extractionthe filtrate was extracted with ethyl acetate (500 mL)
  4. concentrationThe organic layer was subjected to vacuum concentration
  5. distillationto vacuum distillation at 132-135° C.

Sources & evidence

ORD record
ord-fc9b9235d9cf49359251140b795631d9
Source dataset
uspto-grants-2010_06
Patent number
US07728152B2

Reaction notes

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