1,1,3-Trichloropropene → 2-Trifluoromethyl-4-(3-ethoxyphenoxy)-1-(3,3-dichloro-2-propenyloxy)benzene

HRID 1940238Notes

Reaction equation

HRID 1940238 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH3:18])[CH:11]=2)[CH:6]=[CH:5][C:4]=1[OH:19].[H-].[Na+].[Cl:24][C:25]([Cl:29])=[CH:26][CH2:27]Cl>CN(C)C=O>[F:1][C:2]([F:20])([F:21])[C:3]1[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][CH3:18])[CH:11]=2)[CH:6]=[CH:5][C:4]=1[O:19][CH2:27][CH:26]=[C:25]([Cl:29])[Cl:24]

Participants

5

Reactant 3

HCID 173781,1,3-TrichloropropeneHCID 24758Sodium hydrideHCID 214661922-Trifluoromethyl-4-(3-ethoxyphenoxy)phenol

Product 1

HCID 214663272-Trifluoromethyl-4-(3-ethoxyphenoxy)-1-(3,3-dichloro-2-propenyloxy)benzeneYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution prepared by dissolving 0.44 g of 2-trifluoromethyl-4-(3-ethoxyphenoxy)phenol in 10 ml of N,N-dimethylformamide, 0.062 g of sodium hydride (60% oil-based) was added with stirring under ice cooling. After 10 minutes, a solution prepared by dissolving 0.24 g of 1,1,3-trichloro-1-propene in 5 ml of N,N-dimethylformamide was added dropwise under ice cooling. After stirring at room temperature for 10 hours, the reaction solution was poured into ice-water, and extracted twice with 50 ml of diethyl ether. Then, the ether layers were combined, washed with water, dried over anhydrous magnesium sulfate and concentrated to give a crude product. This crude product was subjected to silica gel chromatography to give 0.37 g of 2-trifluoromethyl-4-(3-ethoxyphenoxy)-1-(3,3-dichloro-2-propenyloxy)benzene, yield 62%; nD23.6 1.5369.

Workup

  1. customTo a solution prepared
  2. additionwas added
  3. customa solution prepared
  4. additionwas added dropwise under ice cooling
  5. stirringAfter stirring at room temperature for 10 hours
  6. extractionextracted twice with 50 ml of diethyl ether
  7. washwashed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. customto give a crude product

Sources & evidence

ORD record
ord-8857529bba804ba29a8861703ca2dbd8
Source dataset
uspto-grants-1997_12
Patent number
US05698702

Reaction notes

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