Benzoic Acid → 2,2-diethoxyethyl Benzoate

HRID 13679

Reaction equation

HRID 13679 reaction equation
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5]Cl)[CH3:2].[C:10]([OH:18])(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O.CN(C=O)C>[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

8

Reactant 4

HCID 243Benzoic AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 121282-Chloro-1,1-diethoxyethane

Product 1

HCID 118172582,2-diethoxyethyl BenzoateYield 56%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Chloroacetaldehyde diethyl acetal (2.00 g), benzoic acid (2.16 g), potassium iodide (0.27 g), potassium carbonate (1.11 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 thereby yielded the target compound (1.74 g) in a yield of 56%.

Workup

  1. temperatureby refluxing
  2. filtrationAfter filtration
  3. customthe organic layer was separated
  4. concentrationwas subjected to vacuum concentration

Sources & evidence

ORD record
ord-5ddedaa9d9e64079942ac7ae57726df1
Source dataset
uspto-grants-2010_06
Patent number
US07728152B2

Linked notes

Loading…