2,3-Dimethoxy-5-methyl-6-[(morpholin-4-yl)methyl]benzene-1,4-diol → 2,3-Dimethoxy-5-methyl-6-morpholinomethyl-1,4-benzoquinone

HRID 580235Notes

Reaction equation

HRID 580235 reaction equation
[CH3:1][O:2][C:3]1[C:9]([O:10][CH3:11])=[C:8]([OH:12])[C:7]([CH3:13])=[C:6]([CH2:14][N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:4]=1[OH:5]>[Ag]=O>[CH3:1][O:2][C:3]1[C:4](=[O:5])[C:6]([CH2:14][N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)=[C:7]([CH3:13])[C:8](=[O:12])[C:9]=1[O:10][CH3:11]

Participants

3

Reactant 1

HCID 135185542,3-Dimethoxy-5-methyl-6-[(morpholin-4-yl)methyl]benzene-1,4-diol

Product 1

HCID 135185422,3-Dimethoxy-5-methyl-6-morpholinomethyl-1,4-benzoquinoneYield 50.4%

Reagents, catalysts & solvents 1

HCID 92152Silver(II) oxideCatalyst

Procedure

Silver oxide (15 g) was added to a solution of 2,3-dimethoxy-5-methyl-6-morpholinomethylhydroquinone (9 g) as obtained in Reference Example 8 in ether-dioxane (5:2, 70 ml) and the mixture was stirred at room temperature for 1.5 hours. The filtrate was treated in the conventional manner and the residue was recrystallized from ethyl acetate-hexane to give 2,3-dimethoxy-5-methyl-6-morpholinomethyl-1,4-benzoquinone (4.5 g), melting at 60°-62° C.

Workup

  1. additionThe filtrate was treated in the conventional manner
  2. customthe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b0bb647c07fe426aac04b29a0921faa4
Source dataset
uspto-grants-1988_06
Patent number
US04751303

Reaction notes

Loading…