Propionic Acid → 2(3H)-Benzoxazolone, 6-(1-oxopropyl)-

HRID 1619937Notes

Reaction equation

HRID 1619937 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[O:10].[C:11](O)(=[O:14])[CH2:12][CH3:13]>O>[C:11]([C:7]1[CH:8]=[CH:9][C:4]2[NH:3][C:2](=[O:10])[O:1][C:5]=2[CH:6]=1)(=[O:14])[CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 1032Propionic AcidHCID 60432(3H)-Benzoxazolone

Product 1

HCID 30429472(3H)-Benzoxazolone, 6-(1-oxopropyl)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

1000 g polyphosphoric acid are taken at 50° C., 100 g (740 mmol) 2-benzoxazolinone and 80 mL (1.07 mol) propionic acid are added and then the mixture is stirred for 2 h at 90° C. The reaction mixture is cooled to 50° C. and while being cooled it is combined with 1500 mL cold H2O. H2O phase is decanted off and the whole process is repeated twice more with 1500 mL H2O. Then the solid is suction filtered, triturated with diethyl ether/EtOH, suction filtered and washed with diethyl ether.

Workup

  1. customare taken at 50° C.
  2. temperatureThe reaction mixture is cooled to 50° C.
  3. temperaturewhile being cooled it
  4. customH2O phase is decanted off
  5. filtrationfiltered
  6. customtriturated with diethyl ether/EtOH, suction
  7. filtrationfiltered
  8. washwashed with diethyl ether

Sources & evidence

ORD record
ord-1a6f27d3dc634aad962171d43697eb20
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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