Quinizarin → 2-Methoxybenzene-1,4-diol

HRID 2306905Notes

Reaction equation

HRID 2306905 reaction equation
C1C=CC2C(=O)[C:14]3[C:9](=[C:10]([OH:18])[CH:11]=[CH:12][C:13]=3[OH:17])C(=O)C=2C=1.[C:19]([O-])([O-])=[O:20].[K+].[K+]>C1C=CC=CC=1.[Ag]=O>[CH3:19][O:20][C:14]1[CH:9]=[C:10]([OH:18])[CH:11]=[CH:12][C:13]=1[OH:17]

Participants

5

Reactant 2

HCID 6688QuinizarinHCID 11430Potassium Carbonate

Product 1

HCID 699882-Methoxybenzene-1,4-diolYield 99%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 241BenzeneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 1.00 g (7.10 mmol) of methoxyhydroquinone (3), 2.50 g (10.7 mmol) of silver oxide, and 1.20 g (8.50 mmol) of K2CO3 in 50 mL of benzene was stirred under argon at 25° C. for 3 h, the mixture was filtered through Celite, and washed with 5 mL of dichloromethane. The filtrate was concentrated to give 0.970 g (99% yield) of methoxybenzoquinone (6): 1H NMR d 6.72 (s, 2H), 5.95 (s, 1H), 3.84 (s, 3H). 13CNMR d 187.4, 181.6, 137.1, 134.4, 111.5, 107.6, 56.2. This material was used in the next step without purification.

Workup

  1. filtrationthe mixture was filtered through Celite
  2. washwashed with 5 mL of dichloromethane
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-6897fdf5ac824d89aab4fbde174586f0
Source dataset
uspto-grants-2004_12
Patent number
US06828450B2

Reaction notes

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