Dimethylformamide → 3,5-Dichloro-4-(3-(4-ethoxybenzoyloxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)-benzene

HRID 363072

Reaction equation

HRID 363072 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:14][CH2:15][CH:16]=[C:17]([Cl:19])[Cl:18])[CH:5]=[C:6]([Cl:13])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11]Br.[CH2:20]([O:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=1)[CH3:21].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:1][C:2]1[CH:3]=[C:4]([O:14][CH2:15][CH:16]=[C:17]([Cl:19])[Cl:18])[CH:5]=[C:6]([Cl:13])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][O:29][C:27](=[O:28])[C:26]1[CH:25]=[CH:24][C:23]([O:22][CH2:20][CH3:21])=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 120934-Ethoxybenzoic acidHCID 108840691-[4-(3,3-Dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]-3-bromopropane

Product 1

HCID 542144263,5-Dichloro-4-(3-(4-ethoxybenzoyloxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)-benzeneYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a reaction vessel were placed 0.29 g of 3,5-dichloro-4-(3-bromopropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene, 0.12 g of 4-ethoxybenzoic acid, 0.12 g of potassium carbonate and 10 ml of N,N-dimethylformamide, followed by stirring at room temperature for 12 hours. The reaction mixture was poured into water, and extracted twice with 50 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.30 g of 3,5-dichloro-4-(3-(4-ethoxybenzoyloxy)propyloxy)-1-(3,3-dichloro-2-propenyloxy)-benzene (86% yield), nD24.0 1.5715.

Workup

  1. customIn a reaction vessel were placed
  2. extractionextracted twice with 50 ml of diethyl ether
  3. washThe combined ether layer was washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto obtain a crude product

Sources & evidence

ORD record
ord-0f9ee30d16594025b234ac6543505638
Source dataset
uspto-grants-1999_02
Patent number
US05872137

Linked notes

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