Ethylparaben → HCID 135760589, compound

HRID 1614321Notes

Reaction equation

HRID 1614321 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=O)=[CH:4][CH:3]=1.[O-]CC.[Na+].O[NH:18][C:19](=[NH:22])[CH2:20][CH3:21]>C(O)C>[CH2:20]([C:19]1[N:22]=[C:6]([C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:12][CH:11]=2)[O:8][N:18]=1)[CH3:21]

Participants

5

Reactant 3

HCID 8434EthylparabenHCID 2723922Sodium ethoxideHCID 178458070HCID 178458070, compound

Product 1

HCID 135760589HCID 135760589, compoundYield 22.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a mixture of 29.9 parts of ethyl 4-hydroxybenzoate and 316 parts of ethanol there were added portionwise 35.6 parts of sodiumethoxide. After stirring for 1/2 hour at room temperature, there was added dropwise a solution of 31.7 parts of N-hydroxypropanimidamide in 79 parts of ethanol. Stirring was continued for 1/2 hour at room temperature and overnight at reflux temperature. The reaction mixture was evaporated and the residue was taken up in water. After neutralizing with acetic acid, the precipitate was filtered off and dried. It was purified by column chromatography (HPLC; silica gel; CH2Cl2 /CH3OH 99:1). The eluent of the desired fraction was evaporated and the residue was stirred in petroleumether. The precipitate was filtered off and dried, yielding 7.56 parts (22.1%) of 4-(3-ethyl-1,2,4-oxadiazol-5-yl)phenol; mp. 137.7° C. (interm. 6).

Workup

  1. stirringStirring
  2. waitwas continued for 1/2 hour at room temperature and overnight
  3. temperatureat reflux temperature
  4. customThe reaction mixture was evaporated
  5. filtrationthe precipitate was filtered off
  6. customdried
  7. customIt was purified by column chromatography (HPLC; silica gel; CH2Cl2 /CH3OH 99:1)
  8. customThe eluent of the desired fraction was evaporated
  9. stirringthe residue was stirred in petroleumether
  10. filtrationThe precipitate was filtered off
  11. customdried

Sources & evidence

ORD record
ord-224a83374717443d836e5fc6df745932
Source dataset
uspto-grants-1993_03
Patent number
US05196535

Reaction notes

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