Acetic Acid → HCID 18317013, compound

HRID 276147Notes

Reaction equation

HRID 276147 reaction equation
[C:1]1([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.[BrH:16].O.[CH3:18][C:19](O)=O>>[Br:16][CH:19]([C:11]1[CH:10]=[CH:9][C:8]([O:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:13][CH:12]=1)[CH3:18]

Participants

6

Reactant 5

HCID 176Acetic Acid2×HCID 260Hydrogen BromideHCID 712FormaldehydeHCID 962WaterHCID 7583Diphenyl Ether

Product 1

HCID 18317013HCID 18317013, compound

Conditions

Temperature
60 °C

Procedure

Into 100 mL of glacial HOAc was dissolved 34 g (0.2 Mole) of diphenyl ether. To the stirred solution was added 6.78 g (0.22 Mole) paraformaldehyde and 40 mL of 31% solution of HBr in HOAc. The reaction was heated 48 hours at 60° C. and then poured into cold water with stirring. The mixture was extracted with EtOAc and the resulting organic layer was washed with water, dried over Na2SO4, and evaporated under vacuum to give 50 g of crude 1-bromethyl-4-phenoxybenzene as an oil, which was used in the subsequent reaction without additional purification.

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washthe resulting organic layer was washed with water
  3. dry with materialdried over Na2SO4
  4. customevaporated under vacuum

Sources & evidence

ORD record
ord-f81ad1a402524fd58d765446343aec1b
Source dataset
uspto-grants-2002_03
Patent number
US06353128B1

Reaction notes

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