Potassium Carbonate → 1-Benzoyloxy-4-(2-chlorobenzyloxy)-3,5-dichlorobenzene

HRID 363093Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2.27 g of 4-benzoyloxy-2,6-dichlorophenol, 1.29 g of 2-chlorobenzyl chloride, 1.21 g of potassium carbonate and 50 ml of N,N-dimethylformamide was stirred at 80° C. for 6 hours. The reaction mixture was cooled to room temperature, poured in ice water, and extracted twice with 50 ml of diethyl ether. The combined ether layer was washed with water, and dried with anhydrous magnesium sulfate, followed by removal of the solvent by distillation under reduced pressure. The residue was subjected to silica gel chromatography, which afforded 2.87 g of 1-benzoyloxy-4-(2-chlorobenzyloxy)-3,5-dichlorobenzene (88% yield).

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted twice with 50 ml of diethyl ether
washThe combined ether layer was washed with water
dry with materialdried with anhydrous magnesium sulfate
customfollowed by removal of the solvent by distillation under reduced pressure

Sources & evidence

ORD record: ord-ef446e9598384de0bc34a1635cdb1e3f
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05872137

Reaction notes

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