Chloroacetic Acid → HCID 86735096, compound

HRID 1731150Notes

Reaction equation

HRID 1731150 reaction equation
[P:1]([O-:32])([O:23][C:24]1[CH:29]=[C:28]([CH3:30])[CH:27]=[C:26]([CH3:31])[CH:25]=1)([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=2)=[O:13])=[CH:6][C:5]=1[O:21][CH3:22])=[O:2].[Na+:33].[O-]CC.[Na+].Cl[CH2:39][C:40]([OH:42])=[O:41]>C(O)C>[P:1]([O-:32])([O:23][C:24]1[CH:29]=[C:28]([CH3:30])[CH:27]=[C:26]([CH3:31])[CH:25]=1)([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:39][C:40]([O-:42])=[O:41])[CH:15]=2)=[O:13])=[CH:6][C:5]=1[O:21][CH3:22])=[O:2].[Na+:33].[Na+:33]

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 2723922Sodium ethoxideHCID 86735098HCID 86735098, compound

Product 1

HCID 86735096HCID 86735096, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 22.5 g sodium 4-(3-(3-hydroxyphenyl)-3-oxopropyl)-2-methoxyphenyl 3,5-dimethylphenyl phosphate (see Example 6) and 1000 ml of 0.22 M sodium ethoxide kept under nitrogen, 5.7 g of chloroacetic acid in 50 ml anhydrous ethanol is added dropwise with stirring and the mixture being kept boiling. After all of the acid is added the refluxing is continued for one hour. The reaction mixture is cooled and sodium chloride is removed by filtration. The solvent is evaporated under vacuum, and the residue is dissolved in water, acidified with 2 M hydrochloric acid and extracted with ethyl acetate. The organic layer is washed with saturated sodium sulphate solution. Water is added and pH adjusted to 7 with 2 M sodium hydroxide. The water layer is freeze-dried giving disodium 4-(3-(3-carboxylatomethoxyphenyl)-3-oxopropyl)-2-methoxypenyl 3,5-dimethylphenyl phosphate.

Workup

  1. additionAfter all of the acid is added the refluxing
  2. temperatureThe reaction mixture is cooled
  3. customsodium chloride is removed by filtration
  4. customThe solvent is evaporated under vacuum
  5. dissolutionthe residue is dissolved in water
  6. extractionextracted with ethyl acetate
  7. washThe organic layer is washed with saturated sodium sulphate solution
  8. additionWater is added
  9. dry with materialThe water layer is freeze-dried

Sources & evidence

ORD record
ord-bc07814b814e44488f9cb1aa35d1af53
Source dataset
uspto-grants-1976_11
Patent number
US03995033

Reaction notes

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