Benzoic Acid → 3,5-Dichloro-4-(3-benzoyloxypropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

HRID 1280237Notes

Reaction equation

HRID 1280237 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([Cl:12])=[CH:10][C:9]([O:13][CH2:14][CH:15]=[C:16]([Cl:18])[Cl:17])=[CH:8][C:7]=1[Cl:19].[C:20]([OH:28])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:19][C:7]1[CH:8]=[C:9]([O:13][CH2:14][CH:15]=[C:16]([Cl:18])[Cl:17])[CH:10]=[C:11]([Cl:12])[C:6]=1[O:5][CH2:4][CH2:3][CH2:2][O:28][C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 108840691-[4-(3,3-Dichloroprop-2-enyloxy)-2,6-dichlorophenoxy]-3-bromopropane

Product 1

HCID 184300283,5-Dichloro-4-(3-benzoyloxypropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzeneYield 95.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

First, 11.1 g of 1-(3-bromopropyloxy)-2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)benzene, 3.31 g of benzoic acid, and 50 ml of N,N-dimethylformamide were placed in a reaction vessel, to which 3.90 g of potassium carbonate was added. After stirring at room temperature for 24 hours, the reaction mixture was poured into water, and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate, and concentrated to give a crude product. this crude product was subjected to silica gel chromatography, which afforded 11.6 g (yield, 95%) of 3,5-dichloro-4-(3-benzoyloxypropyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene.

Workup

  1. additionwas added
  2. extractionextracted twice with diethyl ether
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto give a crude product

Sources & evidence

ORD record
ord-c1c00b0567b043c3855ec0dba5236974
Source dataset
uspto-grants-2002_09
Patent number
US06448444B1

Reaction notes

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