Acetic Acid → HCID 10797539, compound

HRID 1967094Notes

Reaction equation

HRID 1967094 reaction equation
[C-:1]#[N:2].[K+].[C:4]1([CH:14]=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1.C(O)(=O)C>CCOCC>[OH:15][CH:14]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)[C:1]#[N:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 61951-NaphthaldehydeHCID 9032Potassium Cyanide

Product 1

HCID 10797539HCID 10797539, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of potassium cyanide in ether (100 mL) at 0° C. was added dropwise a mixture of 1-naphthalenecarboxaldehyde (1.56 g, 10 mmol) and acetic acid (1.41 g, 23.5 mmol) in ether (10 mL). The resulting mixture was warmed to 25° C. for 20 h, the precipitate was filtered and the filtrate was concentrated affording the title compound as a clear oil (1.67 g, 9.14 mmol, 91%): LCMS (ES) m/z 184 (M+H)+.

Workup

  1. filtrationthe precipitate was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7accfdd574f34acd8362ca0c60fd1453
Source dataset
uspto-grants-2013_04
Patent number
US08420690B2

Reaction notes

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