Menadiol → 1,4-Naphthoquinone

Reaction equation

[C:1]1([OH:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([OH:11])=[CH:3][CH:2]=1.OC1C2C(=CC=CC=2)C(O)=CC=1C>>[C:4]1(=[O:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1](=[O:12])[CH:2]=[CH:3]1

Participants

Reactant 2

HCID 10209Menadiol

HCID 113051,4-Naphthalenediol

Product 1

HCID 85301,4-NaphthoquinoneYield 93%

Procedure

Using the same procedure, napthalene- 1,4-diol and 1,4-dihydroxy-2-methyl-naphthalene were oxidized to obtain a 93% yield of 1,4-naphthoquinone and a 97% yield of 2-methyl-1,4-naphthoquinone, respectively.

Sources & evidence

ORD record: ord-52f71c34f2f04ae1a9274cc5665b661b
Source dataset: uspto-grants-1976_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03941811

Reaction notes

Loading…