1-(1-Methyl-2-propenyloxy)-5-methyl-2-nitrobenzene → 2-(1-Methyl-2-propenyl)-3-methyl-6-nitrophenol

HRID 637626

Reaction equation

HRID 637626 reaction equation
CC([O:5][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:7]=1[N+:13]([O-:15])=[O:14])C=C>CCOCC>[CH3:8][CH:7]([C:11]1[C:10]([CH3:12])=[CH:9][CH:8]=[C:7]([N+:13]([O-:15])=[O:14])[C:6]=1[OH:5])[CH:6]=[CH2:11]

Participants

3

Reactant 1

HCID 135602931-(1-Methyl-2-propenyloxy)-5-methyl-2-nitrobenzene

Product 1

HCID 202555762-(1-Methyl-2-propenyl)-3-methyl-6-nitrophenol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

197 g of 1A was placed in a flask, which then was purged with nitrogen, and a slow stream of nitrogen was passed through the system while the 1A was heated gradually. At about 160° C., an exothermic reaction began, and the temperature rose to 220° C. The mixture was contained with cooling, then heated at 185°-200° C. for 1.5 hours, diluted with ether, and filtered. The solvent was evaporated from the filtrate to give crude 2-(1-methyl-2-propenyl)-3-methyl-6-nitrophenol (1B), as a dark syrup.

Workup

  1. customwhich then was purged with nitrogen
  2. temperaturewas heated gradually
  3. customAt about 160° C., an exothermic reaction
  4. customrose to 220° C
  5. temperaturewith cooling
  6. temperatureheated at 185°-200° C. for 1.5 hours
  7. filtrationfiltered
  8. customThe solvent was evaporated from the filtrate

Sources & evidence

ORD record
ord-b2473424328c41298f4115eb9e87fbd2
Source dataset
uspto-grants-1985_12
Patent number
US04558040

Linked notes

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