Potassium Iodide → HCID 14661618, compound

HRID 2108089Notes

Reaction equation

HRID 2108089 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:11])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Br[CH2:13][CH2:14][CH2:15][C:16]([O:18]CC)=[O:17].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:11][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 162513,4-DimethoxyphenolHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 14661618HCID 14661618, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3,4-dimethoxyphenol (10 g), ethyl 4-bromo-butyrate (15.2 g), anhydrous potassium carbonate (11.7 g), potassium iodide (1.5 g) and N,N-dimethylformamide (40 ml) is stirred for 15 hours at 60° to 70° C. The reaction mixture is poured into ice-water and extracted with ethyl acetate. The organic layer is washed with water, dried, and concentrated under reduced pressure. The residue is dissolved in methanol (30 ml), to the solution is added a 2.5N aqueous solution of sodium hydroxide (67 ml), and the mixture is stirred for 40 mintues at 50° to 60° C. The reaction mixture is concentrated under reduced pressure. To the concentrate is added water, and the mixture is acidified (pH 3) with dilute hydrochloric acid, followed by extraction with ethyl acetate. The organic layer is washed with water, dried, and concentrated under reduced pressure. The residue is recrystallized from ethyl acetate - hexane to give 4-(3,4-dimethoxyphenyloxy)butyric acid as colorless prisms (12.5 g). To polyphosphoric acid (60 g) is added 4-(3,4-dimethoxyphenyloxy)butyric acid (6.0 g) obtained above, and the mixture is stirred for 30 minutes at 100° C. The reaction mixture is poured into ice-water and extracted with ethyl acetate. The organic layer is washed with water, dried, and concentrated. The residue is recrystallized from ethyl acetate - hexane to give 7,8-dimethoxy-3,4-dihydro-1benzoxepin-5(2H)-one as colorless prisms, m.p. 87°-88° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue is dissolved in methanol (30 ml), to the solution
  6. additionis added a 2.5N aqueous solution of sodium hydroxide (67 ml)
  7. stirringthe mixture is stirred for 40 mintues at 50° to 60° C
  8. concentrationThe reaction mixture is concentrated under reduced pressure
  9. additionTo the concentrate is added water
  10. extractionfollowed by extraction with ethyl acetate
  11. washThe organic layer is washed with water
  12. customdried
  13. concentrationconcentrated under reduced pressure
  14. customThe residue is recrystallized from ethyl acetate - hexane

Sources & evidence

ORD record
ord-b74c809c61e04b7f99521a0b041df95c
Source dataset
uspto-grants-1990_06
Patent number
US04937246

Reaction notes

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