Propionic anhydride → HCID 53765861, compound

HRID 2413350Notes

Reaction equation

HRID 2413350 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=2)=[CH:4][N:3]=1.[C:17]([O-:21])(=[O:20])[CH2:18][CH3:19].[Na+].C(OC(=O)CC)(=O)CC>>[CH3:19][C:18](=[CH:13][C:12]1[CH:15]=[CH:16][C:9]([O:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[N:3][CH:4]=2)=[CH:10][CH:11]=1)[C:17]([OH:21])=[O:20]

Participants

4

Reactant 3

HCID 31263Propionic anhydrideHCID 2723816Sodium PropionateHCID 13392574HCID 13392574, compound

Product 1

HCID 53765861HCID 53765861, compoundYield 52.3%

Procedure

A mixture of 5 g of 4-(2-methyl-5-pyridyloxy)benzaldehyde, 5 g of sodium propionate and 35 ml of propionic anhydride was stirred for 3 hours at a temperature of 150° to 155° C. and then concentrated under reduced pressure. Water was added to the mixture which was then heated to crystallize the product. The resulting crystals were separated by filtration, washed with water and recrystallized from a mixture of acetic acid and water to obtain 3.3 g (52% yield) of 2-methyl-3-[4-(2-methyl-5-pyridyloxy)phenyl]propenoic acid as colorless needles having a melting point of 211°-213° C. Recrystallization from a mixture of methanol and isopropyl alcohol yielded colorless prisms having a melting point of 211°-214° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionWater was added to the mixture which
  3. temperaturewas then heated
  4. customto crystallize the product
  5. customThe resulting crystals were separated by filtration
  6. washwashed with water
  7. customrecrystallized from a mixture of acetic acid and water

Sources & evidence

ORD record
ord-1ce29e572c274ac6b39d41227e9a66e3
Source dataset
uspto-grants-1985_01
Patent number
US04496735

Reaction notes

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