Hydrochloric Acid → 8-Cyano-octanoic acid

HRID 2263675Notes

Reaction equation

HRID 2263675 reaction equation
[C:1]([C:3]([OH:5])=[O:4])#N.[C:6]([CH2:8][CH2:9][C:10]1C=C[C:13](C(O)=O)=[CH:12][CH:11]=1)#[N:7].BrCCCCCCCC(O)=O.[C-]#N.[Na+].Cl.C#N>CO.O.CCOC(C)=O>[C:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:1][C:3]([OH:5])=[O:4])#[N:7]

Participants

10

Reactant 6

HCID 313Hydrochloric Acid2×HCID 768Hydrogen CyanideHCID 8929Sodium CyanideHCID 5482758-Bromooctanoic acidHCID 9812747Carbonocyanidic AcidHCID 1987919655584-01-5

Product 1

HCID 110843008-Cyano-octanoic acidYield 74%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

The preparation of the cyano-carboxylic acid representing substrate B10 was adapted from a procedure for the preparation of 4-(2-cyanoethyl)benzoic acid (Delia, T. J., Baumann, M., Bunker, A. Heterocycles, 35, 1397-1410 (1993)). To 501 mg (2.25 mmol) of 8-bromooctanoic acid in 7.0 mL of methanol was added 520 mg NaCN (10.6 mmol) in 2.0 mL H2O. The solution was heated at reflux for 2.5 h. After cooling to 25° C., the solution was acidified to pH˜1.5 with concentrated HCl (caution: HCN gas evolves with the addition of HCl) and diluted with 40 mL EtOAc. The resulting suspension was washed twice with 15 mL H2O. The organic layer was dried by filtration through MgSO4, and the solvent was removed in vacuo to afford 282 mg (74%) of a light brown oil. The 1H NMR spectrum agreed with previously reported data in Cotarca et al. Synthesis 1997, 328-332.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 2.5 h
  3. washThe resulting suspension was washed twice with 15 mL H2O
  4. dry with materialThe organic layer was dried by filtration through MgSO4
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-bf4dae2888a34d50bc8b16151956da22
Source dataset
uspto-grants-2010_12
Patent number
US07851658B2

Reaction notes

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