Ammonium Chloride → HCID 54224598, compound

HRID 652314Notes

Reaction equation

HRID 652314 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11](O)[C:12](Cl)([Cl:17])[C:13]([F:16])([F:15])[F:14].[Cl-].[NH4+]>C(O)C.[Zn]>[CH3:10][O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[CH:11]=[C:12]([Cl:17])[C:13]([F:16])([F:15])[F:14]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 13799280HCID 13799280, compound

Product 1

HCID 54224598HCID 54224598, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

96.5 g (0.266 mole) of 1,3-dimethoxy-2-(1-hydroxy-2,2-dichloro-3,3,3-trifluoro-propyl)-benzene are dissolved in 1,000 ml of ethanol in a 1.5 l sulfonating flask with a thermometer, condenser and bubble counter, and 30 g (0.56 mole) of ammonium chloride are added. Zinc activated according to Fieser & Fieser (36.9 g=0.564 mole) is added in portions to the resulting brownish suspension, the reaction temperature rising to 42°. Stirring is continued overnight and the grey-yellow reaction mixture is then poured onto ice-water and extracted with ether and the extract is washed with water (3×) and brine, dried over magnesium sulfate and evaporated. 1,3-Dimethoxy-2-(2-chloro-3,3,3-trifluoroprop-1-enyl)-benzene (yield: 94%) is obtained as a reddish oil.

Workup

  1. additionare added
  2. additionis added in portions to the resulting brownish suspension
  3. customrising to 42°
  4. additionthe grey-yellow reaction mixture is then poured onto ice-water
  5. extractionextracted with ether
  6. washthe extract is washed with water (3×) and brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-2b3b5dbc5dab444ebc9136ceceda0c79
Source dataset
uspto-grants-1987_06
Patent number
US04670604

Reaction notes

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