Potassium Hydroxide → 3-(5-Methyl-2-phenyl-4-oxazolyl)propionic acid

HRID 2121693Notes

Reaction equation

HRID 2121693 reaction equation
[OH-:1].[K+].CCCCC[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[N:15].[CH2:16]([OH:18])[CH3:17].[OH2:19]>>[CH3:17][C:16]1[O:18][C:14]([C:13]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:15][C:8]=1[CH2:9][CH2:10][C:11]([OH:19])=[O:1]

Participants

4

Reactant 3

HCID 14797Potassium HydroxideHCID 17092DodecanenitrileHCID 19096565Water ethanol

Product 1

HCID 120932643-(5-Methyl-2-phenyl-4-oxazolyl)propionic acid

Procedure

KOH (13g, 235 mmol) was added to a mixture of ethanol/water (100 mL/100 mL) containing nitrile 1-2 (12.4 g, 58.68 mmol) and refluxed for 8 hours. Ethanol was removed in vacuo and the residue was acidified to pH=2 with aqueous HCl. The precipitated solid was filtered, washed with water, and dried in a vacuum oven overnight. The recoverd 13.5 g of acid 1-3 was used in the following step with no further purification. NMR CDCl3 (δ): 7.97 (2H, m); 7.45 (3H, m); 2.84 (4H, m); 2.35 (3H, s). M+1=232.1

Workup

  1. temperaturerefluxed for 8 hours
  2. customEthanol was removed in vacuo
  3. filtrationThe precipitated solid was filtered
  4. washwashed with water
  5. customdried in a vacuum oven overnight
  6. customThe recoverd 13.5 g of acid 1-3 was used in the following step with no further purification

Sources & evidence

ORD record
ord-1f8bf8fa613c4ee99042beca0ed92ca6
Source dataset
uspto-grants-2004_02
Patent number
US06696474B2

Reaction notes

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