Sodium Hydroxide → HCID 20345938, compound

HRID 838866Notes

Reaction equation

HRID 838866 reaction equation
[C:1]([C:5]1[CH:22]=[C:21]([CH3:23])[C:8]([CH2:9][CH:10]([C:16]([O:18]CC)=[O:17])[C:11]([O:13]CC)=[O:12])=[C:7]([CH3:24])[C:6]=1[OH:25])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.O>[C:1]([C:5]1[CH:22]=[C:21]([CH3:23])[C:8]([CH2:9][CH:10]([C:11]([OH:13])=[O:12])[C:16]([OH:18])=[O:17])=[C:7]([CH3:24])[C:6]=1[OH:25])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 20345925HCID 20345925, compound

Product 1

HCID 20345938HCID 20345938, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

35 grams of the compound of Example 14 was dissolved in 125 ml of methanol together with 12.3 grams of sodium hydroxide dissolved in 50 ml of water and heated at reflux for 6 hours. After removal of most of the methanol by distillation at reduced pressure, 300 ml of water was added and stirred to yield a turbid solution which was clarified by filtration. The clear filtrate was extracted with ether, and the ether extract washed with water and dried over anhydrous sodium sulfate. After removal of the ether by distillation at reduced pressure, the glassy residue was crystallized from 1,2-dichloroethane yielding white crystals melting at 174°.

Workup

  1. temperatureheated
  2. temperatureat reflux for 6 hours
  3. customAfter removal of most of the methanol
  4. distillationby distillation at reduced pressure, 300 ml of water
  5. additionwas added
  6. customto yield a turbid solution which
  7. filtrationwas clarified by filtration
  8. extractionThe clear filtrate was extracted with ether
  9. extractionthe ether extract
  10. washwashed with water
  11. dry with materialdried over anhydrous sodium sulfate
  12. customAfter removal of the ether
  13. distillationby distillation at reduced pressure
  14. customthe glassy residue was crystallized from 1,2-dichloroethane yielding white crystals melting at 174°

Sources & evidence

ORD record
ord-668be6d580a441fcbb4f73162b0a10ad
Source dataset
uspto-grants-1978_06
Patent number
US04093618

Reaction notes

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