Formaldehyde → Ethyl 2-methylidenebutanoate

HRID 362440Notes

Reaction equation

HRID 362440 reaction equation
[CH3:1][CH2:2][CH:3](P(OCC)(OCC)=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:17]([O-])([O-])=O.[K+].[K+].C=O.O>CCOCC>[CH2:17]=[C:3]([CH2:2][CH3:1])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 229053Ethyl 2-(diethoxyphosphoryl)butanoate

Product 1

HCID 291416Ethyl 2-methylidenebutanoateYield 87%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5.0 g (0.019 mol) of triethyl 2-phosphonobutyrate, 5.5 g (0.039 mol) of K2CO3, 6.2 g (0.076 mol) of 37% aqueous formaldehyde solution, and 15 mL of water was heated to about 80° C. for about 45 min. After cooling to RT, 75 mL of ether was added and the organic layer was separated, washed with brine (1×20 mL), dried (MgSO4), and filtered. The ether was carefully removed by distillation, leaving behind 2.1 g (87%) of the title compound as a clear oil which was used directly without further purification. 1H NMR (CDCl3): 67 1.01 (3H, t, J=7), 1.24 (3H, t, J=7), 2.26 (2H, q, J=7), 4.14 (2H, q, J=7), 5.45 (1H, s), 6.06 (1H, s).

Workup

  1. temperatureAfter cooling to RT
  2. customthe organic layer was separated
  3. washwashed with brine (1×20 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe ether was carefully removed by distillation

Sources & evidence

ORD record
ord-b86d1ac0d50847d384b8902fb40aaab5
Source dataset
uspto-grants-1999_02
Patent number
US05869511

Reaction notes

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