O-Cresol → HCID 21191818, compound

HRID 399784Notes

Reaction equation

HRID 399784 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 is stirred for 5 hours at room temperature (20° C.). The reaction mixture is 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 suction filtered. There is obtained 73 g (0.300 mol=88%) of the title compound as a colorless solid.

Workup

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

Sources & evidence

ORD record
ord-1696be035e0546ffba184f3e4d9d6d43
Source dataset
uspto-grants-1998_10
Patent number
US05824705

Reaction notes

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