Hydrochloric Acid → Valeric acid, 5-cyano-

HRID 1421642Notes

Reaction equation

HRID 1421642 reaction equation
[NH4+].[C:2]([CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O-:10])=[O:9])#[N:3].Cl>>[C:2]([CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9])#[N:3]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 19044055HCID 19044055, compound

Product 1

HCID 199926Valeric acid, 5-cyano-Yield 95%

Procedure

200-mL portion of the filtrate of the product mixture described above, containing the 5-cyanopentanoic acid ammonium salt (1.13 M), was adjusted to pH 2.5 with 6 N HCl, then saturated with sodium chloride and extracted with 4×200 mL of ethyl ether. The combined ether extracts were dried over magnesium sulfate, filtered, and the solvent removed by rotary evaporation at reduced pressure. Remaining ether was removed by stirring the colorless liquid at room temperature under high vacuum (60 millitorr) for 5 h to yield 27.32 g (95% isolated yield) of 5-cyanopentanoic acid. The 5-cyanopentanoic acid was then distilled under vacuum (75 millitorr) at 110-112° C. without decomposition.

Workup

  1. extractionsaturated with sodium chloride and extracted with 4×200 mL of ethyl ether
  2. dry with materialThe combined ether extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent removed by rotary evaporation at reduced pressure
  5. customRemaining ether was removed

Sources & evidence

ORD record
ord-fe101e27c1b049c5ba228c84ee672503
Source dataset
uspto-grants-2000_06
Patent number
US06077955

Reaction notes

Loading…