Ethylparaben → HCID 135760589, compound

HRID 1460206Notes

Reaction equation

HRID 1460206 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 were added portionwise 35.6 parts of sodium ethoxide. 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. 27).

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-97e52a578c8249cd888a01e1407d25cf
Source dataset
uspto-grants-1991_12
Patent number
US05070090

Reaction notes

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