o-Xylyl bromide → 2-(2-Methylbenzyloxy)-acetophenone

HRID 1195918Notes

Reaction equation

HRID 1195918 reaction equation
[OH:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH3:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20]Br>C(O)C>[CH3:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH2:20][O:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 6992o-Xylyl bromideHCID 11430Potassium CarbonateHCID 68490alpha-Hydroxyacetophenone

Product 1

HCID 538898952-(2-Methylbenzyloxy)-acetophenoneYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

102 g (0.75 mol) of 2-hydroxyacetophenone and 102 g (0.75 mol) of potassium carbonate in 500 ml of absolute ethanol are initially taken. 139 g (0.75 mol) of 2-methylbenzyl bromide are added dropwise and the mixture is refluxed for 10 h. The mixture is cooled and filtered under suction, after which the filtrate is evaporated down. The crude product is recrystallized from diethyl ether. 106 g (59%) of product are obtained as crystals (mp.=53°-55° C.).

Workup

  1. temperaturethe mixture is refluxed for 10 h
  2. temperatureThe mixture is cooled
  3. filtrationfiltered under suction
  4. customafter which the filtrate is evaporated down
  5. customThe crude product is recrystallized from diethyl ether

Sources & evidence

ORD record
ord-260ec844d7294184a2ce3d4db9931734
Source dataset
uspto-grants-1992_05
Patent number
US05112862

Reaction notes

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