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1,1,1-Trichloro-2,2,2-trifluoroethane → 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(3,3-dichloro-4,4,4-trifluoro-2-hydroxybutyloxy)butyloxy)benzene

HRID 369667
Notes
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Reaction equation

HRID 369667 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([O:17][CH2:18][CH:19]=[C:20]([Cl:22])[Cl:21])[CH:14]=[C:13]([Cl:23])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][CH2:10][CH:11]=[O:12].[Cl:24][C:25](Cl)([Cl:30])[C:26]([F:29])([F:28])[F:27]>[Zn].CN(C)C=O>[Cl:1][C:2]1[CH:16]=[C:15]([O:17][CH2:18][CH:19]=[C:20]([Cl:22])[Cl:21])[CH:14]=[C:13]([Cl:23])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][CH2:10][CH:11]([OH:12])[C:25]([Cl:30])([Cl:24])[C:26]([F:29])([F:28])[F:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 96351,1,1-Trichloro-2,2,2-trifluoroethaneHCID 538269084-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde

Product 1

HCID 232824133,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(3,3-dichloro-4,4,4-trifluoro-2-hydroxybutyloxy)butyloxy)benzeneYield 63.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst
HCID 6228
Dimethylformamide
Solvent

Procedure

To a mixture of 2.01 g of 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde, 1.31 g of zinc dust and 10 ml of N,N-dimethylformamide was added 4.12 g of 1,1,1-trichlorotrifluoroethane. After stirring at room temperature for 1.5 hours, the reaction mixture was filtered. The filtrate was poured into 20 ml of diluted hydrochloric acid and extracted twice with 50 ml of ethyl acetate. The ethyl acetate layers were combined, washed with water, dried over magnesium sulfate and then evaporated to give a crude product. The crude product was subjected to silica gel chromatography, which afforded 1.76 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(3,3-dichloro-4,4,4-trifluoro-2-hydroxybutyloxy)butyloxy)benzene (yield, 63%), nD24.2 1.5188.

Workup

  1. filtrationthe reaction mixture was filtered
  2. additionThe filtrate was poured into 20 ml of diluted hydrochloric acid
  3. extractionextracted twice with 50 ml of ethyl acetate
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customto give a crude product

Sources & evidence

ORD record
ord-0618dde99335441b96a472b8e46bca52
Source dataset
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06140274

Reaction notes

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