Catechol → 4-Nitrocatechol

HRID 258965Notes

Reaction equation

HRID 258965 reaction equation
C1(C(=CC=CC=1)O)O.C(OC1C(=CC=CC=1)OC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C([O:41][C:42]1[C:43](=[CH:53][C:54]([N+:57]([O-:59])=[O:58])=[CH:55][CH:56]=1)[O:44]C(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>>[N+:57]([C:54]1[CH:53]=[C:43]([OH:44])[C:42](=[CH:56][CH:55]=1)[OH:41])([O-:59])=[O:58]

Participants

4

Reactant 3

HCID 289CatecholHCID 69514o-Phenylene dibenzoateHCID 214251854-Nitropyrocatechol dibenzoate

Product 1

HCID 35051094-NitrocatecholYield 50%

Procedure

Further, the 3,4-dialkoxyanilines of formula I are obtained according to the invention in a yield of about 70% or more of the theoretical amount calculated on pyrocatechol whereas according to a known method comprising dibenzoylation of pyrocatechol, nitration of the pyrocatechol dibenzoate, hydrolysis 4-nitropyrocatechol dibenzoate, successive introduction of alkyl groups R1 and R2 into 4-nitropyrocatechol and reduction of 3,4-dialkoxy-nitrobenzene the 3,4dialkoxyanilines of formula I are obtained in a yield of less than 50% of the theoretical amount calculated on pyrocatechol.

Sources & evidence

ORD record
ord-b15851a34739407f8d29910316699482
Source dataset
uspto-grants-1977_07
Patent number
US04035423

Reaction notes

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