4-Aminophenol → 4-(1H-1,2,3,4-tetrazol-1-yl)phenol

To a stirred solution of p-amino-phenol (0.1 mol) in glacial acetic acid (140 ml) at 70-75° under nitrogen atmosphere was added triethylorthoformate (0.1 mol). The mixture was stirred at this temperature for 4 h, then, sodium azide (0.32 mol) was added portionwise and the reaction was continued for 18 h, cooled to room temperature and poured into ice water (400 ml) and extracted with diethyl ether (3×400 ml) and ethyl acetate (1×400 ml), dried (MgSO4), filtered and concentrated to give a dark brown residue which was triturated with 200 ml of a mixture of ethanol:diethyl ether (1:1 v/v) and filtered to afford the title compound in 30% yield.

1. waitthe reaction was continued for 18 h
2. extractionextracted with diethyl ether (3×400 ml) and ethyl acetate (1×400 ml)
3. dry with materialdried (MgSO4)
4. filtrationfiltered
5. concentrationconcentrated
6. customto give a dark brown residue which
7. customwas triturated with 200 ml of a mixture of ethanol:diethyl ether (1:1 v/v)
8. filtrationfiltered

ORD record

ord-53f140dcf3da4e959a2ab144e43febf6

Source dataset

uspto-grants-2000_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06020346