Potassium Carbonate → Ethyl 2-[4-(para-chlorobenzoyl)-phenoxy]-propionate

HRID 616050Notes

Reaction equation

HRID 616050 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:16])[C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH:24]([CH3:30])[C:25]([O:27][CH2:28][CH3:29])=[O:26]>CC(CC(C)C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:24]([CH3:30])[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:11][CH:10]=2)=[O:16])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 1235044-Hydroxy-4'-chlorobenzophenone

Product 1

HCID 20143873Ethyl 2-[4-(para-chlorobenzoyl)-phenoxy]-propionate

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

0.75 mole (175 g) of 4'-chloro-4-hydroxy-benzophenone, 1.5 l of methylisobutyl ketone, 0.975 mole (134 g) of K2CO3 and 0.8 mole (145 g) of ethyl 2-bromopropionate are placed in a 2-liter flask. The mixture is heated at reflux for 8 hours with vigorous agitation whereupon the reaction mixture is cooled and filtered on a Buchner funnel. The solvent is then evaporated under vacuum and the residue distilled; the desired ester is recovered at 198° to 201° C under 0.1 mm of mercury. Yield 190 g (76%).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 8 hours with vigorous agitation whereupon the reaction mixture
  3. temperatureis cooled
  4. filtrationfiltered on a Buchner funnel
  5. customThe solvent is then evaporated under vacuum
  6. distillationthe residue distilled
  7. customthe desired ester is recovered at 198° to 201° C under 0.1 mm of mercury

Sources & evidence

ORD record
ord-f8fbc4b0c9fa4e9ea6efee93531a4565
Source dataset
uspto-grants-1978_02
Patent number
US04072705

Reaction notes

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