Hydrochloric Acid → HCID 53432669, compound

HRID 2181395Notes

Reaction equation

HRID 2181395 reaction equation
[C:1]([C:3](=[CH:10][CH:11]([CH3:13])[CH3:12])[CH2:4][C:5]([O:7]CC)=[O:6])#[N:2].O.[OH-].[Li+].Cl>O1CCCC1.O>[C:1]([C:3](=[CH:10][CH:11]([CH3:13])[CH3:12])[CH2:4][C:5]([OH:7])=[O:6])#[N:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 85054034Ethyl 3-cyano-5-methyl-3-hexenoate

Product 1

HCID 53432669HCID 53432669, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-cyano-5-methylhex-3-enoate (mixture of E and Z isomers) and lithium hydroxide hydrate are suspended in a mixture of tetrahydrofuran and water. The slurry is vigorously stirred for 4 hours at room temperature. The mixture is acidified to pH 2 (3N HCl) and extracted into ethyl acetate (3×150 mL). The combined organic layers are dried (MgSO4), and the solvent is removed in vacuo to give crude 3-cyano-5-methylhex-3-enoic acid. The crude acid is dissolved in ethyl acetate (400 mL), and a solution of tert-butylamine in ethyl acetate (20 mL) is added. The temperature of the solution rises approximately 10° C. as a mass of white crystalline solid precipitates. The product is collected by filtration and dried in vacuo. Yield 22.15 g, 97.9 mmol, 89%.

Workup

  1. extractionextracted into ethyl acetate (3×150 mL)
  2. dry with materialThe combined organic layers are dried (MgSO4)
  3. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-647237047c1f41d68933fd006cbcaddd
Source dataset
uspto-grants-2005_05
Patent number
US06891059B2

Reaction notes

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