Sodium Hydroxide → HCID 15057647, compound

HRID 654031Notes

Reaction equation

HRID 654031 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:15]=[C:14]([F:16])[CH:13]=[C:7]([C:8]([O:10]CC)=[O:9])[C:6]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:2].[OH-].[Na+]>C(O)C>[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:15]=[C:14]([F:16])[CH:13]=[C:7]([C:8]([OH:10])=[O:9])[C:6]=1[O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15057646HCID 15057646, compound

Product 1

HCID 15057647HCID 15057647, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

25.63 g (74 mmol) of 2-benzyloxy-5-fluoroisophthalic acid diethyl ester is dissolved in 200 ml of dry ethanol with exclusion of moisture and a solution of 1.48 g of sodium hydroxide in 50 ml of ethanol is instilled into this solution in the course of 2 hours at room temperature. The monosodium salt gradually precipitates. When the instillation is completed, it is stirred for 1 hour more, the precipitate is suctioned off and the filtrate is concentrated by evaporation to about half. In this process additional monosodium salt precipitates which is also suctioned off. The two filter residues are combined, suspended in water and the suspension is acidified with concentrated hydrochloric acid. The monoacid is shaken out with ethyl acetate, the ethyl acetate solution is dried on sodium sulfate, filtered and concentrated by evaporation. The solid residue is dried in a vacuum at 50° C. 14.93 g (46.92 mmol)=63.4% of the theoretical yield is obtained as a partially crystalline, partially amorphous solid.

Workup

  1. customis instilled into this solution in the course of 2 hours at room temperature
  2. customThe monosodium salt gradually precipitates
  3. concentrationthe filtrate is concentrated by evaporation to about half
  4. customIn this process additional monosodium salt precipitates which
  5. filtrationThe two filter residues
  6. stirringThe monoacid is shaken out with ethyl acetate
  7. dry with materialthe ethyl acetate solution is dried on sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated by evaporation
  10. customThe solid residue is dried in a vacuum at 50° C
  11. custom14.93 g (46.92 mmol)=63.4% of the theoretical yield
  12. customis obtained as a partially crystalline, partially amorphous solid

Sources & evidence

ORD record
ord-c033da2be8f94c4bb2ab90dbcc6f88d5
Source dataset
uspto-grants-1992_07
Patent number
US05130119

Reaction notes

Loading…