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

HRID 1387243Notes

Reaction equation

HRID 1387243 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-di-methylforrnamide. After stiring at room temperature for 15 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 44.1 g of 4-(3,3-dichloro-2-propenyloxy)phenyl benzoate (96% yield).

Workup

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

Sources & evidence

ORD record
ord-cbc1a5bcd84d432c9a74bcae61022661
Source dataset
uspto-grants-2001_07
Patent number
US06268313B1

Reaction notes

Loading…