Benzyl Chloride → 4-Benzyl-2-bromo-6-methylphenol

HRID 371518

Reaction equation

HRID 371518 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[C:6]([CH3:9])[CH:5]=[CH:4][CH:3]=1.[CH2:10](Cl)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>[Zn]>[Br:1][C:2]1[C:7]([OH:8])=[C:6]([CH3:9])[CH:5]=[C:4]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 7503Benzyl ChlorideHCID 110953292-Bromo-6-methylphenol

Product 1

HCID 134880864-Benzyl-2-bromo-6-methylphenolYield 41.2%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Conditions

Temperature
150 °C

Procedure

500 g of the so-obtained 6-bromo-2-methylphenol, together with 10 g zinc shavings, are heated to about 100° C. Within 20 minutes 453 g benzyl chloride are added dropwise with stirring and under moisture exclusion. For a further 12 minutes the reaction mixture is heated to 150° C. It is then held a total of 5 hours at the temperature of 150° C. After cooling, the zinc is separated. The reaction product is distilled in a vacuum at 0.03 up to 0.04 Torr. 305 g 6-bromo-2-methyl-4-benzylphenol are obtained as a weakly yellowish, oily liquid, which is nearly odorless.

Workup

  1. customa total of 5 hours
  2. customat the temperature of 150° C
  3. temperatureAfter cooling
  4. customthe zinc is separated
  5. distillationThe reaction product is distilled in a vacuum at 0.03 up to 0.04 Torr

Sources & evidence

ORD record
ord-351fb69f2d704fa980601c8c6ac9aaf1
Source dataset
uspto-grants-1985_07
Patent number
US04532367

Linked notes

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