Formaldehyde → HCID 69150705, compound

HRID 1179275Notes

Reaction equation

HRID 1179275 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9](P(OCC)(OCC)=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11].C=O.[C:25](=O)([O-])[O-].[K+].[K+]>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9](=[CH2:25])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 86602108HCID 86602108, compound

Product 1

HCID 69150705HCID 69150705, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

To a stirred mixture of ethyl 3-(2-chlorophenyl)-2-(diethoxyphosphoryl)propanoate (step 1, 14.6 g, 41.9 mmol) and 37% formaldehyde in water (20 mL) was added a solution of potassium carbonate (17.4 g) in water (80 mL) at the room temperature and the mixture was stirred for 6 h at 90° C. After cooling to room temperature, the mixture was extracted with diethyl ether (300 mL), and then the organic layer was washed with brine (100 mL), dried over magnesium sulfate, and evaporated. The residue was purified by column chromatography on silica gel (300 g) eluting with hexane/ethyl acetate (30/1) to afford 6.57 g (70%) of the title compound as a colorless oil:

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with diethyl ether (300 mL)
  3. washthe organic layer was washed with brine (100 mL)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel (300 g)
  7. washeluting with hexane/ethyl acetate (30/1)

Sources & evidence

ORD record
ord-e500a2b2f86b4a6c92176d838c5b63e6
Source dataset
uspto-grants-2007_10
Patent number
US07279486B2

Reaction notes

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