Carbon Tetrachloride → Butyl ether

HRID 1730206Notes

Reaction equation

HRID 1730206 reaction equation
[N+]([C:4]1[CH:5]=[CH:6][C:7]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])=C(C)C=1)([O-])=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl.BrN1C(=O)CCC1=O>O>[CH2:7]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:6][CH2:5][CH3:4]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 7187Benzoyl Peroxide2×HCID 67184N-bromobutanimideHCID 706687061-Butoxy-2-methyl-4-nitrobenzene

Product 1

HCID 8909Butyl ether

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred and gently refluxing mixture of 256 parts of butyl (5-nitro-o-tolyl) ether, 1 part of benzoyl peroxide and 4800 parts of anhydrous carbon tetrachloride is added, over a one-day period, a mixture of 213.6 parts of N-bromosuccinimide and 1 part of benzoyl peroxide. Upon completion, stirring at gentle reflux is continued overnight. The reaction mixture is cooled and water is added. The organic layer is separated, washed with water, dried, filtered and evaporated. The oily residue is crystallized on standing overnight in 2-propanol, yielding 189.7 parts of (α-bromo-5-nitroo-tolyl) butyl ether; mp. 64° C.

Workup

  1. temperaturegently refluxing
  2. additionis added, over a one-day period
  3. stirringUpon completion, stirring
  4. temperatureat gentle reflux
  5. temperatureThe reaction mixture is cooled
  6. customThe organic layer is separated
  7. washwashed with water
  8. customdried
  9. filtrationfiltered
  10. customevaporated
  11. customThe oily residue is crystallized
  12. waiton standing overnight in 2-propanol

Sources & evidence

ORD record
ord-53d1771c49b644ff8220b1e22bce9323
Source dataset
uspto-grants-1976_11
Patent number
US03991202

Reaction notes

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