Methanol → HCID 18475331, compound

HRID 2187347Notes

Reaction equation

HRID 2187347 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-bd3409541e604d0c95ce869bf35f17f1
Source dataset
uspto-grants-2002_06
Patent number
US06410486B1

Reaction notes

Loading…