Water → 1-(2-Methyl-2-phenylpropoxy)-4-nitrobenzene

HRID 1679504Notes

Reaction equation

HRID 1679504 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](Cl)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:11][C:12]([CH3:21])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:13][OH:14].[H-].[Na+].O>CS(C)=O>[CH3:11][C:12]([CH3:21])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:13][O:14][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 74741-Chloro-4-nitrobenzeneHCID 24758Sodium hydrideHCID 219535beta,beta-Dimethylbenzeneethanol

Product 1

HCID 128250041-(2-Methyl-2-phenylpropoxy)-4-nitrobenzeneYield 72%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In 200 ml of dimethylsulfoxide are dissolved 23 g of 4-nitrochlorobenzene and 25 g of 2,2-dimethyl-2-phenylethylalcohol. To this solution is added 4 g of sodium hydride is added with stirring. After 24 hours stirring at room temperature and another 30 minutes stirring at 60° C, 500 ml of water is added and the mixture is extracted with ether. The extract is washed with water, dried and the solvent is evaporated. Recrystallization of the residue from 200 ml of methanol, gives 28.5 g of 4-(2,2-dimethyl-2-phenylethyloxy)nitrobenzene, melting point: 79°-80° C.

Workup

  1. additionis added
  2. stirringAfter 24 hours stirring at room temperature and another 30 minutes
  3. stirringstirring at 60° C
  4. extractionthe mixture is extracted with ether
  5. washThe extract is washed with water
  6. customdried
  7. customthe solvent is evaporated
  8. customRecrystallization of the residue from 200 ml of methanol

Sources & evidence

ORD record
ord-a0a5b1197f904bc5a824d4b3fdd8d39f
Source dataset
uspto-grants-1978_03
Patent number
US04080505

Reaction notes

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