Benzyl Bromide → 1-[5-(Benzyloxy)-2-hydroxyphenyl]ethan-1-one

HRID 1967184Notes

Reaction equation

HRID 1967184 reaction equation
[C:1]([C:4]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=1[OH:6])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[Na+]>CC(CC(C)C)=O.O>[OH:6][C:5]1[CH:7]=[CH:8][C:9]([O:11][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:10][C:4]=1[C:1](=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 102792-AcetylhydroquinoneHCID 11430Potassium CarbonateHCID 14798Sodium Hydroxide

Product 1

HCID 128709281-[5-(Benzyloxy)-2-hydroxyphenyl]ethan-1-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
60 °C

Procedure

20 kg (131.4 mol) 2-acetyl-hydroquinone 6a are dissolved in 150 l methylisobutylketone and combined with 19.98 kg (144.6 mol) potassium carbonate. At 60° C., 22.48 kg (131.5 mol) benzyl bromide are added. The reaction mixture is stirred for 20 hours at 60° C. The reaction mixture is cooled to 25° C. and the solid is filtered off. The filtrate is washed twice with a solution of 0.96 kg (11.8 mol) sodium hydroxide solution (50%) and 60 l water at 25° C. The methylisobutylketone is largely distilled off in vacuo, and the residue is dissolved in 80 l methanol at 60° C. The solution is cooled to 0° C. and stirred for 1 hour at this temperature to complete the crystallisation.

Workup

  1. temperatureThe reaction mixture is cooled to 25° C.
  2. filtrationthe solid is filtered off
  3. distillationThe methylisobutylketone is largely distilled off in vacuo
  4. dissolutionthe residue is dissolved in 80 l methanol at 60° C
  5. temperatureThe solution is cooled to 0° C.
  6. stirringstirred for 1 hour at this temperature
  7. customthe crystallisation

Sources & evidence

ORD record
ord-b9096d3cae004575b2c90012072d4cc9
Source dataset
uspto-grants-2013_04
Patent number
US08420809B2

Reaction notes

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