Hydrochloric Acid → HCID 15234816, compound

HRID 1108194Notes

Reaction equation

HRID 1108194 reaction equation
[NH4+].[C:2]([C:4](=[CH2:10])[CH2:5][CH2:6][C:7]([O-:9])=[O:8])#[N:3].Cl>>[C:2]([C:4](=[CH2:10])[CH2:5][CH2:6][C:7]([OH:9])=[O:8])#[N:3]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 131720854HCID 131720854, compound

Product 1

HCID 15234816HCID 15234816, compoundYield 60%

Conditions

Temperature
-78 °C

Procedure

A 100-mL portion of the filtrate containing the 4-cyano-4-pentenoic acid ammonium salt product mixture described above was adjusted to pH 2.7 with 6 N HCl, then saturated with sodium chloride and extracted with 4×100 mL of ethyl ether. The combined organic extracts were dried over magnesium sulfate, filtered, and the volume of the combined extracts reduced to 100 mL by rotary evaporation at reduced pressure at 28° C. To the ether solution was added 200 mL of hexane, and the resulting solution cooled to -78° C. The resulting white solid which crystallized was isolated by rapid vacuum filtration and washing with 100 mL of cold (5° C.) hexane. Residual solvent was removed under high vacuum (150 millitorr) to yield 9.80 g (60% isolated yield) of 4-cyano-4-pentenoic acid (m.p. 26.5-27.0° C., stored at -20° C.).

Workup

  1. extractionsaturated with sodium chloride and extracted with 4×100 mL of ethyl ether
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe volume of the combined extracts reduced to 100 mL by rotary evaporation at reduced pressure at 28° C
  5. additionTo the ether solution was added 200 mL of hexane
  6. customThe resulting white solid which crystallized
  7. customwas isolated by rapid vacuum filtration
  8. washwashing with 100 mL of cold (5° C.) hexane
  9. customResidual solvent was removed under high vacuum (150 millitorr)

Sources & evidence

ORD record
ord-4a5e9864aa8f4ee28885be9995b5ca0e
Source dataset
uspto-grants-2000_05
Patent number
US06066490

Reaction notes

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