Water → 2-[(4-tert-Butylphenyl)methyl]-4-chloro-6-methylphenol

HRID 371522

Reaction equation

HRID 371522 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.[C:10]([C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1)([CH3:13])([CH3:12])[CH3:11].O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:18][C:17]2[CH:20]=[CH:21][C:14]([C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:15][CH:16]=2)[C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 148554-Chloro-2-methylphenolHCID 88198Benzene, 1-(chloromethyl)-4-(1,1-dimethylethyl)-

Product 1

HCID 714140642-[(4-tert-Butylphenyl)methyl]-4-chloro-6-methylphenol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

106.5 g (0.75 mol) 4-chloro-2-methylphenol and 45.67 g (0.25 mol) 4-tert. butylbenzylchloride are dissolved in 200 ml chloroform, and 22.5 g water-free zinc chloride are added as Friedel-Crafts catalyst. Thereafter the reaction mixture is stirred, whereby indeed at room temperature to the start of the reaction intense gas development, i.e. intense reaction, is to be noted. Subsequently the reaction mixture is stirred at 60° C. 5-6 h and washed three times each with 200 ml water for the purpose of removing the zinc chloride. The organic phase is dried across magnesium sulfate and the chloroform is driven off in a vacuum. At 182°-185° C./0.3 Torr the 4-chloro-2-methyl-6-(4'-tert. butylbenzyl)-phenol distills over as water-clear, viscous, nearly odorless liquid.

Workup

  1. customwhereby indeed at room temperature to the start of the reaction intense gas development, i.e. intense reaction
  2. stirringSubsequently the reaction mixture is stirred at 60° C
  3. wash5-6 h and washed three times each with 200 ml water for the purpose
  4. customof removing the zinc chloride
  5. dry with materialThe organic phase is dried across magnesium sulfate
  6. distillationAt 182°-185° C./0.3 Torr the 4-chloro-2-methyl-6-(4'-tert. butylbenzyl)-phenol distills over as water-clear

Sources & evidence

ORD record
ord-10fcae91893c403881b74948e7c2dc88
Source dataset
uspto-grants-1985_07
Patent number
US04532367

Linked notes

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