Ammonium Chloride → HCID 20396694, compound

HRID 972121Notes

Reaction equation

HRID 972121 reaction equation
[Na].[OH:2][C:3]1[CH:4]=[C:5]([OH:10])[CH:6]=[C:7]([Br:9])[CH:8]=1.Cl[CH2:12][CH:13]([O:16][CH3:17])[O:14][CH3:15].[Cl-].[NH4+]>O.CN(C)C=O>[CH3:15][O:14][CH:13]([O:16][CH3:17])[CH2:12][O:2][C:3]1[CH:4]=[C:5]([OH:10])[CH:6]=[C:7]([Br:9])[CH:8]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 609862-Chloro-1,1-dimethoxyethaneHCID 5573835-bromobenzene-1,3-diolHCID 5360545Sodium

Product 1

HCID 20396694HCID 20396694, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

The monosodium salt of 3-hydroxy-5-bromophenol (0.05 mole) and dimethylformamide (75 ml) are charged under nitrogen gas into a glass reaction vessel equipped with a mechanical stirrer, thermometer and additional funnel. The mixture is stirred until dissolved, and 1-chloro-2,2-dimethoxyethane (0.05 mole) is added dropwise over a period of about 20 minutes. After the addition is completed, the reaction mixture is heated at about 90° C. with stirring for a period of about 48 hours. After this time water (200 ml) is added, and the reaction mixture is neutralized with ammonium chloride. The reaction mixture is then extracted with chloroform, and the organic phase is separated from the aqueous phase. The organic phase is then stripped of solvent, leaving an oil. This oil is distilled under reduced pressure to yield the desired product 3-(2,2-dimethoxyethoxy)-5-bromophenol.

Workup

  1. customequipped with a mechanical stirrer
  2. dissolutionuntil dissolved
  3. additionAfter the addition
  4. stirringwith stirring for a period of about 48 hours
  5. extractionThe reaction mixture is then extracted with chloroform
  6. customthe organic phase is separated from the aqueous phase
  7. customleaving an oil
  8. distillationThis oil is distilled under reduced pressure

Sources & evidence

ORD record
ord-f2f32b4e5f9b4b75a2f97061a36b42f6
Source dataset
uspto-grants-1979_07
Patent number
US04163112

Reaction notes

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