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

HRID 369660
Notes
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Reaction equation

HRID 369660 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([O:18][CH2:19][CH:20]=[C:21]([Cl:23])[Cl:22])[CH:15]=[C:14]([Cl:24])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH2:11][CH:12]=O.[Cl:25][C:26](Cl)(Cl)[C:27]([F:30])([F:29])[F:28].C(OC(=O)C)(=O)C>[Zn].CN(C)C=O>[Cl:24][C:14]1[CH:15]=[C:16]([O:18][CH2:19][CH:20]=[C:21]([Cl:22])[Cl:23])[CH:17]=[C:2]([Cl:1])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH2:11]/[CH:12]=[C:26](\[Cl:25])/[C:27]([F:30])([F:29])[F:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 96351,1,1-Trichloro-2,2,2-trifluoroethaneHCID 540452085-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetaldehyde

Product 1

HCID 86755966(Z)-3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(5-(3-chloro-4,4,4-trifluoro-2-butenyloxy)pentyloxy)benzeneYield 14%

Reagents, catalysts & solvents 2

HCID 23994
Zinc
Catalyst
HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1.21 g of 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetaldehyde, 0.57 g of zinc dust and 10 ml of N,N-dimethylformamide was added 0.82 g of 1,1,1-trichlorotrifluoroethane. After stirring at room temperature for 1.5 hours, 0.44 g of acetic anhydride was added. The reaction mixture was stirred at room temperature for 3 hours and then filtered. The filtrate was poured into 20 ml of diluted hydrochloric acid and extracted twice with 50 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 0.21 g of (Z)-3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(5-(3-chloro-4,4,4-trifluoro-2-butenyloxy)pentyloxy)benzene [the integrated CF3 signal ratio of Z/E=94/6 as determined by 19F-NMR (CDCl3 /CFCl3)] (yield, 14%), nD26.5 1.5123.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 hours
  2. filtrationfiltered
  3. additionThe filtrate was poured into 20 ml of diluted hydrochloric acid
  4. extractionextracted twice with 50 ml of diethyl ether
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customto give a crude product

Sources & evidence

ORD record
ord-ea00d6a1397d483481fa7f3186c5f968
Source dataset
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06140274

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes