Phenethyl bromide → HCID 15295878, compound

HRID 1952994Notes

Reaction equation

HRID 1952994 reaction equation
[O-]CC.[Na+].[Na].[OH:6][C:7]1[CH:8]=[CH:9][C:10]([N+:14]([O-:16])=[O:15])=[C:11]([CH3:13])[CH:12]=1.[C:17]1([CH2:23][CH2:24]Br)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[N+:14]([C:10]1[CH:9]=[CH:8][C:7]([O:6][CH2:24][CH2:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][C:11]=1[CH3:13])([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 7666Phenethyl bromide2×HCID 174123-Methyl-4-nitrophenolHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 15295878HCID 15295878, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a sodium ethoxide solution prepared from 15 g (0.652 Mol) of sodium and 500 ml of anhydrous ethanol were added, successively, 100 g (0.653 Mol) of 5-hydroxy-2-nitrotoluene and 90 ml (121.95 g=0.659 Mol) of 2-phenylethylbromide and the mixture was refluxed for 5 hours. A further 50 ml (0.366 Mol) of 2-phenylethylbromide were added and again the mixture was refluxed for 10 hours. The solvent was distilled off in vacuo, the residue was taken up in ether and extracted several times with dilute sodium hydroxide solution. The ethereal phase was evaporated down, the residue was stirred thoroughly with 400 ml of petroleum ether 35/60. The resulting crystals were suction filtered and washed with petroleum ether. Yield: 95.2 g (57% of theory) of slightly yellowish crystals, Mp. 70-72° C. IR (CH2Cl2): 1340, 1515 (NO2) cm-1

Workup

  1. additionwere added
  2. temperatureagain the mixture was refluxed for 10 hours
  3. distillationThe solvent was distilled off in vacuo
  4. extractionextracted several times with dilute sodium hydroxide solution
  5. customThe ethereal phase was evaporated down
  6. filtrationfiltered
  7. washwashed with petroleum ether

Sources & evidence

ORD record
ord-11e669d13e8248039b5901db9d37267a
Source dataset
uspto-grants-2000_09
Patent number
US06114390

Reaction notes

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