Dimethylformamide → 4-(3,3-Dichloro-2-propenyloxy)phenyl benzoate

HRID 618394Notes

Reaction equation

HRID 618394 reaction equation
[C:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:23][C:24]([Cl:28])=[CH:25][CH2:26]Cl.CN(C)C=O>O>[C:1]([O:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:26][CH:25]=[C:24]([Cl:28])[Cl:23])=[CH:14][CH:15]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 173781,1,3-TrichloropropeneHCID 75549p-Hydroxyphenyl benzoate

Product 1

HCID 185046614-(3,3-Dichloro-2-propenyloxy)phenyl benzoateYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reaction vessel was charged with 30.5 g of 4-hydroxyphenyl benzoate, 21.6 g of potassium carbonate, 20.8 g of 1,1,3-trichloropropene and 100 ml of N,N-dimethylformamide. After stirring at room temperature for 15 hours, the reaction mixture was poured into water and extracted twice with 150 ml of diethyl ether. The ether layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated to give a crude product. The crude product was subjected to silica gel chromatography, which afforded 44.1 g of 4-(3,3-dichoro-2-propenyloxy)phenyl benzoate (96% yield).

Workup

  1. extractionextracted twice with 150 ml of diethyl ether
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto give a crude product

Sources & evidence

ORD record
ord-604b67a6ed3a4b89b6d36b1a0edca81b
Source dataset
uspto-grants-1999_09
Patent number
US05952386

Reaction notes

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