Potassium Carbonate → HCID 19017377, compound

HRID 1728307Notes

Reaction equation

HRID 1728307 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:5](=[CH:10][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7].[CH3:16][O:17][C:18]1[CH:29]=[CH:28][C:21]([O:22][CH:23](Br)[CH2:24][CH2:25][CH3:26])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:16][O:17][C:18]1[CH:29]=[CH:28][C:21]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][O:1][C:2]2[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:5](=[CH:10][CH:11]=2)[C:6]([O:8][CH3:9])=[O:7])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 89726Dimethyl 4-hydroxyphthalateHCID 19017378HCID 19017378, compound

Product 1

HCID 19017377HCID 19017377, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

21.0 g (0.1 mol) of dimethyl 4-hydroxyphthalate, 25.9 g (0.1 mol) of p-methoxyphenoxy-l-bromobutane and 100 ml of acetonitrile were put in a 300-ml three-neck flask, and 6.91 g of potassium carbonate was added in three divided portions at two-hour intervals at 70° to 80° C. The reaction system was stirred further for 7 hours under reflux. The system was cooled to room temperature, and the salts formed and acetonitrile were taken out by filtration and distillation, respectively. Ethyl acetate and water were added to the residue, which was then washed well with water. Ethyl acetate was removed by distillation, and the residue was recrystallized from a mixed solvent of hexane/ethyl acetate (6/4, v/v). 28.0 g of the intended product was obtained, having a melting point of 68° C. The yield was 72.0%.

Workup

  1. temperatureunder reflux
  2. customthe salts formed
  3. filtrationacetonitrile were taken out by filtration and distillation
  4. additionEthyl acetate and water were added to the residue, which
  5. washwas then washed well with water
  6. customEthyl acetate was removed by distillation
  7. customthe residue was recrystallized from a mixed solvent of hexane/ethyl acetate (6/4, v/v)

Sources & evidence

ORD record
ord-3e9b70f76d9d481a9c09c6b2668c9aed
Source dataset
uspto-grants-1994_07
Patent number
US05326740

Reaction notes

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