4-Hydroxy-3-methoxybenzonitrile → 3,4-Dihydroxybenzonitrile

HRID 1006705

Reaction equation

C([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12]CC)[C:7]#[N:8])C.COC1C=C(C=CC=1O)C#N.[Br-].[Li+]>>[OH:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[OH:12])[C:7]#[N:8]

Participants

Reactant 3

HCID 781354-Hydroxy-3-methoxybenzonitrile

HCID 82050Lithium Bromide

HCID 129461903,4-Diethoxybenzonitrile

Product 1

HCID 870653,4-DihydroxybenzonitrileYield 79%

Procedure

The preparation was carried out according to the process of Example 2a except that 3,4-diethoxybenzonitrile was used as the starting material instead of 3-methoxy-4-hydroxybenzonitrile, and 2-fold of lithium bromide (162.6 g, 1.88 mole) were added to form the reaction mixture. 3,4-Dihydroxybenzonitrile was obtained as a white solid with a yield of 79% and a purity of greater than 92% as indicated by HPLC analysis.

Workup

customto form the reaction mixture

Sources & evidence

ORD record: ord-59cb6a1788d04c77932ef7acef6dc074
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06790977B2

Linked notes

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