Methanol → HCID 18475331, compound

HRID 1386497Notes

Reaction equation

HRID 1386497 reaction equation
C([C:3]([C:12]#[N:13])([CH:7]([CH:9]1[CH2:11][CH2:10]1)[CH3:8])[C:4]([OH:6])=[O:5])C.CO.[OH-].[Na+]>O1CCCC1>[C:12]([CH:3]([CH:7]([CH:9]1[CH2:10][CH2:11]1)[CH3:8])[C:4]([OH:6])=[O:5])#[N:13]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium Hydroxide2×HCID 18475322HCID 18475322, compound

Product 1

HCID 18475331HCID 18475331, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

39.8 g (0.22 mol) of ethyl 2-cyano-3-cyclopropylbutanoic acid were refluxed for 4 hours in a mixture of in each case 150 ml of methanol, tetrahydrofuran and 2 N sodium hydroxide solution. For working-up, 200 ml of 2 N sodium hydroxide solution were added and the mixture was extracted repeatedly with diethyl ether. The aqueous phase was subsequently acidified by adding hydrochloric acid and also extracted with ether. After this organic phase had been dried and concentrated, 29 g (yield 86%) of 2-cyano-3-cyclopropylbutanoic acid were obtained.

Workup

  1. extractionthe mixture was extracted repeatedly with diethyl ether
  2. additionby adding hydrochloric acid
  3. extractionalso extracted with ether
  4. customAfter this organic phase had been dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b78dc391b4364aec908a771c12cc1c70
Source dataset
uspto-grants-2001_07
Patent number
US06265447B1

Reaction notes

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