Water → HCID 57545186, compound

HRID 1661518Notes

Reaction equation

HRID 1661518 reaction equation
C[O:2][C:3](=[O:25])[CH:4]([C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=1)[O:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH3:14])[CH:9]=[C:8]([O:15][CH2:16][CH3:17])[CH:7]=1.O.C(=O)([O-])[O-].[K+].[K+]>CO>[Br:24][C:21]1[CH:20]=[CH:19][C:18]([CH:4]([O:5][C:6]2[CH:7]=[C:8]([O:15][CH2:16][CH3:17])[CH:9]=[C:10]([O:12][CH2:13][CH3:14])[CH:11]=2)[C:3]([OH:25])=[O:2])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 57545204HCID 57545204, compound

Product 1

HCID 57545186HCID 57545186, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

16.9 g (41.3 mmol) of methyl(4-bromophenyl)-(3,5-diethoxyphenoxy)acetate are dissolved in 80 ml of methanol and 8 ml of water under argon at RT, and 7.99 g (57.8 mmol) of potassium carbonate are added. The mixture is heated under RF for 4 h. After cooling, the precipitate is filtered off, the filtrate is concentrated, the residue is taken up in water and the solution is extracted four times with diethyl ether. The aqueous phase is adjusted to a pH of 2 by adding 10% strength hydrochloric acid and is extracted three times with ethyl acetate, and the combined ethyl acetate phases are washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. 16.1 g (99% of theory) of the product are obtained.

Workup

  1. temperatureThe mixture is heated under RF for 4 h
  2. temperatureAfter cooling
  3. filtrationthe precipitate is filtered off
  4. concentrationthe filtrate is concentrated
  5. extractionthe solution is extracted four times with diethyl ether
  6. additionby adding 10% strength hydrochloric acid
  7. extractionis extracted three times with ethyl acetate
  8. washthe combined ethyl acetate phases are washed with saturated sodium chloride solution
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. custom16.1 g (99% of theory) of the product are obtained

Sources & evidence

ORD record
ord-19482c96379b47138c2ad592573849b3
Source dataset
uspto-grants-2011_10
Patent number
US08030347B2

Reaction notes

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