1,1,1-Trichloro-2,2,2-trifluoroethane → HCID 23282361, compound

HRID 369689

Reaction equation

HRID 369689 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)[C:26](F)([F:28])[F:27].[Cl-].[Al+3].[Cl-].[Cl-]>CN(C)C=O.[Zn]>[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:24])=[C:26]([F:28])[F:27]

Participants

6

Reactant 3

HCID 96351,1,1-Trichloro-2,2,2-trifluoroethaneHCID 6451240Aluminum(III) ChlorideHCID 538269084-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde

Product 1

HCID 23282361HCID 23282361, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6228DimethylformamideSolvent

Procedure

Then, 19.54 g of 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde was dissolved in 200 ml of N,N-dimethylformamide, to which 25.3 g of 1,1,1-trichlorotrifluoroethane, 17.6 g of zinc dust and 2.0 g of aluminum chloride were added. After stirring at room temperature for 1.5 hours, the reaction mixture was filtered. The filtrate was poured into diluted hydrochloric acid and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over magnesium sulfate and then concentrated to give a crude product. The crude product was subjected to silica gel chromatography, which afforded 8.46 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(3-chloro-4,4-difluoro-2-hydoxy-3-butenyloxy)butyloxy)benzene (yield, 38%), nD22.5 1.5302.

Workup

  1. additionwere added
  2. filtrationthe reaction mixture was filtered
  3. additionThe filtrate was poured into diluted hydrochloric acid
  4. extractionextracted twice with diethyl ether
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customto give a crude product

Sources & evidence

ORD record
ord-44e24706c43649f8978e8ee0a1e5db3f
Source dataset
uspto-grants-2000_10
Patent number
US06140274

Linked notes

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