Acetic Anhydride → (Z)-3,5-diethyl-1-(3,3-dichloro-2-propenyloxy)-4-(5-(3-chloro-4,4,4-trifluoro-2-butenyloxy)pentyloxy)benzene

HRID 369669

Reaction equation

HRID 369669 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6](Cl)(Cl)[C:7]([F:10])([F:9])[F:8].[CH2:13]([C:15]1[CH:30]=[C:29]([O:31][CH2:32][CH:33]=[C:34]([Cl:36])[Cl:35])[CH:28]=[C:27]([CH2:37][CH3:38])[C:16]=1[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][CH2:24][CH:25]=O)[CH3:14].C(OC(=O)C)(=O)C>[Zn].CN(C)C=O>[CH2:13]([C:15]1[CH:30]=[C:29]([O:31][CH2:32][CH:33]=[C:34]([Cl:35])[Cl:36])[CH:28]=[C:27]([CH2:37][CH3:38])[C:16]=1[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][CH2:24]/[CH:25]=[C:6](\[Cl:5])/[C:7]([F:10])([F:9])[F:8])[CH3:14]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 96351,1,1-Trichloro-2,2,2-trifluoroethaneHCID 6451240Aluminum(III) ChlorideHCID 537387765-(2,6-Diethyl-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetaldehyde

Product 1

HCID 86755968(Z)-3,5-diethyl-1-(3,3-dichloro-2-propenyloxy)-4-(5-(3-chloro-4,4,4-trifluoro-2-butenyloxy)pentyloxy)benzeneYield 192.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 0.12 g of aluminum chloride and 50 ml of N,N-dimethylformamide was added 3.04 g of 1,1,1-trichlorotrifluoroethane. After stirring at room temperature for 1 hour, 1.21 g of 5-(2,6-diethyl-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetaldehyde was added, and the reaction mixture was further stirred at room temperature for 4 hours, to which 1.38 g of acetic anhydride was added. After stirring at room temperature for 1 hour, 0.88 g of zinc dust was added, and the reaction mixture was stirred at room temperature for 12 hours and filtered. The filtrate was poured into 50 ml of diluted hydrochloric acid and extracted twice with 100 ml of diethyl ether. The diethyl ether 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 2.91 g of (Z)-3,5-diethyl-1-(3,3-dichloro-2-propenyloxy)-4-(5-(3-chloro-4,4,4-trifluoro-2-butenyloxy)pentyloxy)benzene (yield, 72%), nD26.0 1.4958.

Workup

  1. additionwas added
  2. stirringAfter stirring at room temperature for 1 hour
  3. stirringthe reaction mixture was stirred at room temperature for 12 hours
  4. filtrationfiltered
  5. additionThe filtrate was poured into 50 ml of diluted hydrochloric acid
  6. extractionextracted twice with 100 ml of diethyl ether
  7. washwashed with water
  8. dry with materialdried over magnesium sulfate
  9. customevaporated
  10. customto give a crude product

Sources & evidence

ORD record
ord-e8a7db0a2be54d9580a7dbbfe22b336d
Source dataset
uspto-grants-2000_10
Patent number
US06140274

Linked notes

Loading…