HCID 15857768, compound → HCID 10964511, compound

HRID 581649Notes

Reaction equation

HRID 581649 reaction equation
[NH4+].[C:2]([CH:4]([CH2:9][CH3:10])[CH2:5][C:6]([O-:8])=[O:7])#[N:3]>Cl>[C:2]([CH:4]([CH2:9][CH3:10])[CH2:5][C:6]([OH:8])=[O:7])#[N:3]

Participants

3

Reactant 1

HCID 15857768HCID 15857768, compound

Product 1

HCID 10964511HCID 10964511, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
-20 °C

Procedure

A 300-mL portion of the filtrate described above, containing 1.26 M 3-cyanopentanoic acid ammonium salt, was adjusted to pH 2.5 with ca. 60 mL of 6 N HCl, then saturated with sodium chloride and extracted with 4×200 mL of ethyl ether. The combined organic extracts were dried over magnesium sulfate, filtered, and the solvent removed by rotary evaporation at reduced pressure at 28° C. The resulting slightly-yellow viscous oil was stirred under high vacuum (50 millitorr) to remove residual solvent at 28° C., then cooled to -20° C. for 2-3 h to produce 3-cyanopentanoic acid as a crystalline white solid (45.9 g, 96% yield); m.p. 33.0-34.0° C.

Workup

  1. extractionsaturated with sodium chloride and extracted with 4×200 mL of ethyl ether
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent removed by rotary evaporation at reduced pressure at 28° C
  5. customto remove residual solvent at 28° C.

Sources & evidence

ORD record
ord-59ace455653b403f806c3f6d873dfabe
Source dataset
uspto-grants-1999_07
Patent number
US05922589

Reaction notes

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