O-Cresol → HCID 21191818, compound

HRID 1602119Notes

Reaction equation

HRID 1602119 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6]Br)([O-:3])=[O:2].[C:12]1([CH3:19])[C:17]([OH:18])=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH3:19][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=1[O:18][CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 335O-CresolHCID 11430Potassium CarbonateHCID 77569alpha-Bromo-2-nitrotoluene

Product 1

HCID 21191818HCID 21191818, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

75 g (0.347 mol) of 2-nitrobenzyl bromide, 37 g (0.342 mol) of o-cresol and 56 g (0.405 mol) of potassium carbonate in 500 ml of dimethylformamide are stirred for 5 hours at room temperature. The reaction mixture is then diluted with water and the aqueous phase is extracted three times with ether. The ether phase is dried and evaporated down. The crystalline residue is stirred with methanol and filtered off under suction. 73 g (0.300 mol=88%) of the title compound are obtained as a colorless solid. mp.=83° C.

Workup

  1. extractionthe aqueous phase is extracted three times with ether
  2. dry with materialThe ether phase is dried
  3. customevaporated down
  4. filtrationfiltered off under suction

Sources & evidence

ORD record
ord-afa4d896f66d46f4bbaedaacdd8e72e5
Source dataset
uspto-grants-1999_11
Patent number
US05981532

Reaction notes

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