Acetic Acid → HCID 12721726, compound

HRID 1979804Notes

Reaction equation

HRID 1979804 reaction equation
[Na].Cl[CH:3]=[C:4]([Cl:8])[C:5](=[O:7])[CH3:6].[C:9]([OH:12])(=O)[CH3:10].[CH2:13]([OH:15])[CH3:14]>>[Cl:8][CH:4]([C:5](=[O:7])[CH3:6])[CH:3]([O:12][CH2:9][CH3:10])[O:15][CH2:13][CH3:14]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 702Ethanol2×HCID 5360545SodiumHCID 534251373,4-Dichlorobut-3-en-2-one

Product 1

HCID 12721726HCID 12721726, compoundYield 64%

Procedure

To a solution of 2.30 g of sodium metal in 180 ml ethanol, cooled in an ice-bath is added dropwise a solution of 13.90 g (0.10 mole) 1,2-dichloro-1-buten-3-one in 20 ml ethanol. The mixture is stirred for 2 hours, acidified with glacial acetic acid (4 ml) and the precipitated salt removed by filtration, washing with ethanol. The filtrate is concentrated in vacuo, the residue slurried in ethyl ether and filtered to remove salt. The ether is evaporated in vacuo and the residual oil is distilled to yield 12.49 g (64%) of the title compound, B.P. 52° C. at 1.5 torr. 1H-NMR (CDCl3) ppm (delta): 1.17 (t, 3H), 1.22 (t, 3H), 2.30 (s, 3H), 3.63 (m, 4H), 4.18 (d, 1H), 4.68 (d, 1H).

Workup

  1. customthe precipitated salt removed by filtration
  2. washwashing with ethanol
  3. concentrationThe filtrate is concentrated in vacuo
  4. filtrationfiltered
  5. customto remove salt
  6. customThe ether is evaporated in vacuo
  7. distillationthe residual oil is distilled

Sources & evidence

ORD record
ord-93cdd7206e5b410b8e343887b7d91f34
Source dataset
uspto-grants-1984_11
Patent number
US04482723

Reaction notes

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