Ethanol → 5-azidopentanoic Acid

HRID 355228Notes

Reaction equation

HRID 355228 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6]CC#N)=[N+:2]=[N-:3].[OH-:10].[K+].[CH2:12]([OH:14])[CH3:13]>O>[N:1]([CH2:4][CH2:5][CH2:6][CH2:13][C:12]([OH:10])=[O:14])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 32896455-Azidopentanenitrile

Product 1

HCID 111161715-azidopentanoic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

A solution of 5-azidovaleronitrile (12.4 g, 0.1 mol) in ethanol (50 ml) was diluted with water (12 ml) and treated with potassium hydroxide (8.4 g, 0.15 mol). The reaction mixture was refluxed for 18 h, cooled to 23° C. and washed with ether. The aqueous solution was acidified with concentrated hydrochloric acid, saturated with sodium chloride and extracted with ethyl acetate. The organic extracts were combined and dried over anhydrous sodium sulfate. The ethyl acetate was evaporated under reduced pressure and the resulting yellow liquid was distilled under high vacuum; bp 104°-6° C./(0.3 mm); 10.8 g; 87%; ir (neat) νmax : 2095 (N3) and 1708 cm-1 (C=O of carboxylic acid; 1Hmr (CDCl3) δ: 11.63 (1H, s, H of carboxylic acid), 3.3 (2H, m, δ-H), 2.4 (2H, m, α-H) and 2.0-1.2 ppm (4H, β -H and γ-H).

Workup

  1. temperatureThe reaction mixture was refluxed for 18 h
  2. washwashed with ether
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe ethyl acetate was evaporated under reduced pressure
  6. distillationthe resulting yellow liquid was distilled under high vacuum

Sources & evidence

ORD record
ord-b3e3fd87868345bbb4b0c380e84fe550
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

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