4-Methylbenzyl chloride → Pentabromophenyl-(4-methylbenzyl) ether

HRID 441361Notes

Reaction equation

HRID 441361 reaction equation
[CH3:1][O:2][CH2:3][CH2:4]O.[Br:6][C:7]1[C:12](O)=[C:11]([Br:14])[C:10]([Br:15])=[C:9]([Br:16])[C:8]=1[Br:17].[OH-].[Na+].ClC[C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1>O>[Br:6][C:7]1[C:12]([CH:1]([O:2][CH:3]([C:4]2[C:11]([Br:14])=[C:10]([Br:15])[C:9]([Br:16])=[C:8]([Br:17])[C:7]=2[Br:6])[C:22]2[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=2)[C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)=[C:11]([Br:14])[C:10]([Br:15])=[C:9]([Br:16])[C:8]=1[Br:17]

Participants

6

Reactant 4

HCID 77224-Methylbenzyl chlorideHCID 80192-MethoxyethanolHCID 11852PentabromophenolHCID 14798Sodium Hydroxide

Product 1

HCID 88819929Pentabromophenyl-(4-methylbenzyl) ether

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

600 ml. of methyl glycol, 97.75 g (0.2 mole) of pentabromophenol, 8 g (0.2 mole) of sodium hydroxide in 8 ml of water, and 28.12 g (0.2 mole) of 1-chloromethyl-4-methyl-benzene were reacted in the manner previously described. At 65° C. the reaction perceptibly commenced. The ether crystallized in long needles during the refluxing of the mixture. Yield: 96 g (81%), M.P. 194° C. 10 g recrystallized from 300 ml of methoxyethyl chloride had a melting point of 200°-202° C.

Workup

  1. customAt 65° C. the reaction
  2. customThe ether crystallized in long needles during the
  3. temperaturerefluxing of the mixture
  4. custom10 g recrystallized from 300 ml of methoxyethyl chloride

Sources & evidence

ORD record
ord-6130e3548097442cad990338a28660e3
Source dataset
uspto-grants-1977_08
Patent number
US04039587

Reaction notes

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