1,4-Naphthalenediol → 1,4-Naphthoquinone

HRID 1164696Notes

Reaction equation

HRID 1164696 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][CH:3]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([Te:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=O)=[CH:17][CH:16]=1>C(Cl)(Cl)Cl>[CH3:30][O:29][C:26]1[CH:25]=[CH:24][C:23]([Te:21][C:18]2[CH:19]=[CH:20][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)=[CH:28][CH:27]=1.[CH:8]1[CH:7]=[C:6]2[C:11]([C:2]([CH:3]=[CH:4][C:5]2=[O:12])=[O:1])=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 113051,4-NaphthalenediolHCID 3044917Bis(p-methoxyphenyl) telluroxide

Product 2

HCID 85301,4-NaphthoquinoneYield 97%HCID 4605422Benzene, 1,1'-tellurobis[4-methoxy-Yield 56%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1,4-Dihydroxynaphthalene (80 mg, 0.50 mmol) and bis-(p-methoxyphenyl)-telluroxide (196 mg, 0.55 mmol) were stirred in chloroform (4 ml) at room temperature under argon for 1 h. The reaction mixture was concentrated by evaporation of the solvent under reduced pressure and p.l.c. (benzene-ethyl acetate 9:1) gave bis-(p-methoxyphenyl)-telluride (96 mg, 56%) and p-naphthoquinone (77 mg, 97%) as an olive green solid m.p. 122°-125° which on recrystallisation from ethanol gave yellow needles (60 mg, 76%) m.p. 125°-126° (lit., 126) δ(CDCl3) 8.27-7.67 (4H, m), and 7.00 (2H, S).

Workup

  1. concentrationThe reaction mixture was concentrated by evaporation of the solvent under reduced pressure and p.l.c

Sources & evidence

ORD record
ord-ae9f081be80842a1940c73492fb84164
Source dataset
uspto-grants-1983_01
Patent number
US04370497

Reaction notes

Loading…