2,6-Dichlorophenol → 3,5-Dichloro-4-hydroxyphenyl thiocyanate

HRID 1460642Notes

Reaction equation

HRID 1460642 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[OH:9].[S-:10][C:11]#[N:12].[NH4+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([S:10][C:11]#[N:12])[CH:5]=[C:4]([Cl:8])[C:3]=1[OH:9]

Participants

4

Reactant 2

HCID 68992,6-DichlorophenolHCID 15666Ammonium thiocyanate

Product 1

HCID 108894203,5-Dichloro-4-hydroxyphenyl thiocyanateYield 14.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

2,6-Dichlorophenol (100 g, 0.613 mole) and ammonium thiocyanate (102.73 g, 1.350 mole) were mixed in methanol and the solution cooled to 0° C. Chlorine gas was bubbled through the reaction, maintaining the temperature below 10° C. The solution turned a pale yellow color. The reaction was stirred for a total of 3 hours until acidic, at which time ammonia gas was bubbled through and the solution stirred for an additional three hours at 0° to 10° C. The reaction was poured into iced distilled water, and filtered, yielding approximately 20 g of a yellow solid which was dried over night in vacuo. The filtrate was extracted with ethyl acetate, dried over magnesium sulfate and stripped to yield approximately 100 g of crude product. Following purification by chromatography, the material was taken up in 1 liter of toluene, charcoal was added, stirred, filtered, and recrystallized from hexane to yield 55.03 g bf product as a yellow solid. The structure was confirmed by NMR.

Workup

  1. customChlorine gas was bubbled through the reaction
  2. temperaturemaintaining the temperature below 10° C
  3. customwas bubbled through and the solution
  4. stirringstirred for an additional three hours at 0° to 10° C
  5. additionThe reaction was poured
  6. distillationinto iced distilled water
  7. filtrationfiltered

Sources & evidence

ORD record
ord-7865f77384e24aa69208dd396a0db9cb
Source dataset
uspto-grants-1991_12
Patent number
US05071876

Reaction notes

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