Hydrogen Bromide → alpha-Oxo-4-(2-phenylethoxy)-benzeneacetaldehyde

HRID 65213Notes

Reaction equation

HRID 65213 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[CH:12][CH:11]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br.[OH2:20]>CS(C)=O>[O:18]=[C:16]([C:13]1[CH:12]=[CH:11][C:10]([O:9][CH2:1][CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[CH:15][CH:14]=1)[CH:17]=[O:20]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 133400571-[4-(2-Phenylethoxy)phenyl]ethanone

Product 1

HCID 20234168alpha-Oxo-4-(2-phenylethoxy)-benzeneacetaldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
58 °C

Procedure

A 27.7 g portion of 4'-phenethyloxy-acetophenone was dissolved in 200 ml of dimethylsulfoxide. A 39.2 ml portion of 48% hydrobromic acid was added in small portions (exothermic), then the mixture was heated at 58° C. for 17 hours. The mixture was poured into 500 ml of ice and water and the solid was collected, washed with water and dried, giving the desired product as a yellow solid, mp 44°-59° C.

Workup

  1. customthe solid was collected
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-21a127a8b165453f84140b8cd0a4e0c4
Source dataset
uspto-grants-1986_09
Patent number
US04613611

Reaction notes

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