Nitric Acid → 2,3-dimethoxy-6-nitrophenol

HRID 1066555Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[OH:11].[N+:12]([O-])([OH:14])=[O:13].C1(O)C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(O)(=O)C.O>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[C:5]([N+:12]([O-:14])=[O:13])[C:4]=1[OH:11]

Participants

Conditions

Temperature: 5 °C

Procedure

2,3-Dimethoxyphenol (79) (5.00 g, 0.032 mol) was dissolved in glacial acetic acid (50 ml) and the resultant, stirred solution was cooled to 5° C. A cooled (5° C.) mixture of concentrated nitric acid (10 ml) and water (10 ml) was added in one portion to the phenol solution which immediately turned dark red-brown. The mixture was stirred for a further minute and poured into water (200 ml), this solution was neutralised with saturated sodium bicarbonate solution until all effervescense had ceased. The resultant yellow solution was extracted with several portions of diethyl ether until the ether remained almost colourless. The combined extracts were washed with water until the water remained almost colourless, dried (MgSO4) and the ether evaporated off in vacuo to leave a brown oil. This was purified by column chromatography (10% petrol/dichloromethane) to give a bright yellow solid.

Workup

temperatureA cooled
stirringThe mixture was stirred for a further minute
extractionThe resultant yellow solution was extracted with several portions of diethyl ether until the ether
washThe combined extracts were washed with water until the water
dry with materialdried (MgSO4)
customthe ether evaporated off in vacuo
customto leave a brown oil
customThis was purified by column chromatography (10% petrol/dichloromethane)
customto give a bright yellow solid

Sources & evidence

ORD record: ord-29d63292ebbb4c7296b6e3531b8b73e8
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06242636B1

Reaction notes

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