Potassium Carbonate → 3-Chloro-4-methoxymethoxy-5-methyl-1-(3,3-dichloro-2-propenyloxy)benzene

HRID 1356981Notes

Reaction equation

HRID 1356981 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:13])[CH:5]=[C:6]([CH3:12])[C:7]=1[O:8][CH2:9][O:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].[Cl:20][C:21]([Cl:25])=[CH:22][CH2:23]Cl>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([O:13][CH2:23][CH:22]=[C:21]([Cl:25])[Cl:20])[CH:5]=[C:6]([CH3:12])[C:7]=1[O:8][CH2:9][O:10][CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 173781,1,3-TrichloropropeneHCID 185045733-Chloro-4-methoxymethoxy-5-methylphenol

Product 1

HCID 185045973-Chloro-4-methoxymethoxy-5-methyl-1-(3,3-dichloro-2-propenyloxy)benzeneYield 91.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 10 g of 3-chloro-4-methoxymethoxy-5-methylphenol, 7 g of potassium carbonate and 100 ml of N,N-dimethylformamide was added dropwise a solution of 8 g of 1,1,3-trichloro-1-propene dissolved in 30 ml of N,N-dimethylformamide, while stirring at room temperature. After stirring at room temperature for 12 hours, the reaction mixture was poured into ice-water, and extracted twice with 200 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel chromatography, which afforded 14.1 g of 3-chloro-4-methoxymethoxy-5-methyl-1-(3,3-dichloro-2-propenyloxy)benzene (91% yield).

Workup

  1. stirringAfter stirring at room temperature for 12 hours
  2. extractionextracted twice with 200 ml of diethyl ether
  3. washThe combined ether layer was washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e90635eb4804455b9a71ca09b21364b4
Source dataset
uspto-grants-2003_07
Patent number
US06589914B2

Reaction notes

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