Sodium Hydroxide → HCID 14127186, compound

HRID 1196985Notes

Reaction equation

HRID 1196985 reaction equation
[OH-].[Na+].[CH2:3]=[C:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][O:7][C:6]2[CH:15]=[CH:16][C:17]([CH2:19][C:20]([O:22]C)=[O:21])=[CH:18][C:5]1=2>CO>[CH2:3]=[C:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][O:7][C:6]2[CH:15]=[CH:16][C:17]([CH2:19][C:20]([OH:22])=[O:21])=[CH:18][C:5]1=2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10107703HCID 10107703, compound2×

Product 1

HCID 14127186HCID 14127186, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixed solvent of 200 ml of methanol and 50 ml of 2N-aqueous sodium hydroxide solution is added 2.9 g of methyl 11-methylene-6,11-dihydrodibenz[b,e]oxepin-2-acetate (raw material 7, Reference example 7) and the mixture is heated at reflux for two hours. After allowing the mixture to stand for cooling, the mixture is concentrated under reduced pressure, and the pH of the mixture is adjusted to 1.0 with aqueous 4N-hydrochloric acid solution. The mixture is extracted with 500 ml of ethyl acetate, washed with aqueous 1N-hydrochloric acid solution and saturated aqueous sodium chloride solution in order and dried over anhydrous sodium sulfate. The solvent is distilled away under reduced pressure and the resultant crude product is crystallized from hexane to obtain 2.7 g of the desired product as a white solid.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for two hours
  3. temperaturefor cooling
  4. concentrationthe mixture is concentrated under reduced pressure
  5. extractionThe mixture is extracted with 500 ml of ethyl acetate
  6. washwashed with aqueous 1N-hydrochloric acid solution and saturated aqueous sodium chloride solution in order
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent is distilled away under reduced pressure
  9. customthe resultant crude product is crystallized from hexane

Sources & evidence

ORD record
ord-a194203e672f44268e248547af15f19d
Source dataset
uspto-grants-1992_05
Patent number
US05116863

Reaction notes

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