Sodium Hydroxide → HCID 54243608, compound

HRID 1579789Notes

Reaction equation

HRID 1579789 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[C:20]([C:21](=[O:29])[C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[CH:19][CH:18]=[CH:17][C:6]=1[CH2:7][CH:8]([C:14]([O-:16])=[O:15])[C:9]([O:11]CC)=[O:10]>O.CO>[CH3:3][O:4][C:5]1[C:20]([C:21](=[O:29])[C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[CH:19][CH:18]=[CH:17][C:6]=1[CH2:7][CH:8]([C:14]([OH:16])=[O:15])[C:9]([OH:11])=[O:10]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86732900HCID 86732900, compound

Product 1

HCID 54243608HCID 54243608, compoundYield 45.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 86.4 g of sodium hydroxide in 180 ml of water was added with stirring to a suspension of 226.6 g of ethyl 2-methoxy-3-(p-chlorobenzoyl)-benzyl-malonate in 2.8 liters of methanol and the mixture was refluxed for 3 hours and then was cooled to room temperature. The mixture was filtered and the precipitate recovered was washed with methanol, then with ether and dried. The residue was dissolved in 800 ml of water and the solution was washed with ether and acidified to a pH of 1 by addition of 0.5N hydrochloric acid. The acid precipitate formed was extracted with ether and the combined organic phases were washed with water, dried over magnesium sulfate, treated with activated carbon, filtered and evaporated to dryness under reduced pressure. The residue was crystallized from benzene to obtain 96.2 g of 2-methoxy-3-(p-chlorobenzoyl)-benzyl-malonic acid in the form of colorless crystals which melted at 142°C after crystallization from benzene.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. filtrationThe mixture was filtered
  3. customthe precipitate recovered
  4. washwas washed with methanol
  5. dry with materialwith ether and dried
  6. dissolutionThe residue was dissolved in 800 ml of water
  7. washthe solution was washed with ether
  8. additionacidified to a pH of 1 by addition of 0.5N hydrochloric acid
  9. customThe acid precipitate formed
  10. extractionwas extracted with ether
  11. washthe combined organic phases were washed with water
  12. dry with materialdried over magnesium sulfate
  13. additiontreated with activated carbon
  14. filtrationfiltered
  15. customevaporated to dryness under reduced pressure
  16. customThe residue was crystallized from benzene

Sources & evidence

ORD record
ord-f88124fdfb524c1e934f221889eb76a5
Source dataset
uspto-grants-1976_01
Patent number
US03931302

Reaction notes

Loading…