Methyl iodide → 2-Nitro-4-phenylmethoxyanisole

HRID 1090699Notes

Reaction equation

HRID 1090699 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:5]=1[OH:18])([O-:3])=[O:2].[C:19]([O-])([O-])=O.[K+].[K+].CI>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].CC(C)=O>[N+:1]([C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:6][C:5]=1[O:18][CH3:19])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 46066344-(Benzyloxy)-2-nitrophenol

Product 1

HCID 156769762-Nitro-4-phenylmethoxyanisoleYield 804.5%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 180AcetoneSolvent

Procedure

With 82 g (0.335 mole) of 2-nitro-4-phenylmethoxy-phenol, 46 g (0.035 mole) of K2CO3, 83 ml (1.34 moles) of methyl iodide and 2 g of TBAB in 400 ml of acetone were refluxed for 12 hours. The cooled solution was filtered and evaporated. The residue was taken up with methylene chloride, washed with water then dried on sodium sulfate. Evaporation of the solvent gave 73 g (Yield=85%) of 2-nitro-4-phenylmethoxy-anisole.

Workup

  1. filtrationThe cooled solution was filtered
  2. customevaporated
  3. washwashed with water
  4. customthen dried on sodium sulfate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f4ada4b011e347a4923acc7c0253a77d
Source dataset
uspto-grants-1992_01
Patent number
US05082847

Reaction notes

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