Formaldehyde → Ethyl 4-methyl-2-methylenepentanoate

HRID 1058764Notes

Reaction equation

HRID 1058764 reaction equation
C(OP(OCC)([CH:6]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=O)C.C=O.[C:21](=O)([O-])[O-].[K+].[K+].O>C(OCC)C>[CH3:15][CH:13]([CH3:14])[CH2:12][C:6](=[CH2:21])[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 15234297Ethyl 2-diethylphosphono-4-methylpentanoate

Product 1

HCID 10909818Ethyl 4-methyl-2-methylenepentanoateYield 63.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 19 g (67.9 mmol) of ethyl 2-(diethoxyphosphinyl)-4-methylpentanoate, 27 ml (360.3 mmol) of formaldehyde and 28 g (202.6 mmol) of potassium carbonate is maintained at reflux for 3 hours. A mixture of water and diethyl ether is added. The aqueous phase is extracted with diethyl ether. The combined organic phases are washed with water, dried over sodium sulphate, filtered and evaporated under reduced pressure. The residue is distilled under reduced pressure. 6.7 g of product are recovered in the form of an oil (yield=63.3%).

Workup

  1. temperatureis maintained
  2. temperatureat reflux for 3 hours
  3. additionis added
  4. extractionThe aqueous phase is extracted with diethyl ether
  5. washThe combined organic phases are washed with water
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. distillationThe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-c2182c56e34443cb9c1699103aa2f571
Source dataset
uspto-grants-2003_02
Patent number
US06518260B1

Reaction notes

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