Potassium Carbonate → HCID 53641489, compound

HRID 330270Notes

Reaction equation

HRID 330270 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:4]([C:5](OC)=O)[C:3]=1[OH:12].[C:13]([O-])([O-])=O.[K+].[K+].Br[CH2:20][C:21]([O:23][CH3:24])=[O:22]>CC(C)=O>[CH3:13][O:12][C:3]1[C:4](=[CH:9][CH:10]=[CH:11][C:2]=1[Cl:1])[CH:5]=[CH:20][C:21]([O:23][CH3:24])=[O:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 104098Methyl 3-chlorosalicylate

Product 1

HCID 53641489HCID 53641489, compoundYield 116.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A mixture of 3-chlorosalicylic acid (20.2 g, 0.117 mol), Na2SO4 (5.0 g, 0.035 mol), MeOH (100 mL), and saturated methanolic HCl (40 mL) was heated under reflux for 2 days. The mixture was filtered, concentrated, and partitioned between ether and H2O. The organic phase was washed with saturated aqueous NaHCO3, dried (MgSO4) and concentrated to give a yellow oil (17.4 g). A mixture of methyl 3-chlorosalicylate (17.4 g, 0.093 mol), K2CO3 (12.9 g, 0.093 mol), and acetone (100 mL) was heated for 10 minutes. Additional acetone (100 mL) and methyl bromoacetate (14.3 g, 0.093 mol) were added and heating was continued for 18 hours. The mixture was cooled, concentrated, and partitioned between ether and H2O. The organic phase was dried (MgSO4) and concentrated to give a pale yellow oil (24.6 g, 80%).

Workup

  1. temperaturewas heated for 10 minutes
  2. temperatureheating
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated
  5. custompartitioned between ether and H2O
  6. dry with materialThe organic phase was dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0b54c00b9c5f4f9aa38f49e476ac6f20
Source dataset
uspto-grants-1990_01
Patent number
US04895860

Reaction notes

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