4-Hydroxybenzoic acid hydrazide → 4-(5-Methyl-1,3,4-oxadiazol-2-YL)phenol

Reaction equation

[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=1.[C:12](OCC)(OCC)(OCC)[CH3:13]>>[CH3:12][C:13]1[O:7][C:6]([C:5]2[CH:10]=[CH:11][C:2]([OH:1])=[CH:3][CH:4]=2)=[N:8][N:9]=1

Participants

Reactant 2

HCID 17424-Hydroxybenzoic acid hydrazide

HCID 66221Triethyl orthoacetate

Product 1

HCID 51246024-(5-Methyl-1,3,4-oxadiazol-2-YL)phenolYield 99%

Procedure

A mixture of 9.6 parts of 4-hydroxybenzoic acid hydrazide and 44 parts of 1,1',1"-[ethylidynetris(oxy)]trisethane is stirred and refluxed overnight. The precipitated product is filtered off and crystallized from 1-butanol, yielding 10.5 parts (99%) of 4-(5-methyl-1,3,4-oxadiazol-2-yl)phenol; mp. 238.8° C.

Workup

temperaturerefluxed overnight
filtrationThe precipitated product is filtered off
customcrystallized from 1-butanol

Sources & evidence

ORD record: ord-cd252313e6a94ef1942b4287ed627795
Source dataset: uspto-grants-1980_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04218458

Reaction notes

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