Ethanol → HCID 14650456, compound

HRID 1200195Notes

Reaction equation

HRID 1200195 reaction equation
Br[C:2]1([C:8]2[O:9][C:10]3[C:18]([CH2:19][C:20]#N)=[CH:17][CH:16]=[CH:15][C:11]=3[C:12](=[O:14])[CH:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.S(=O)(=O)(O)[OH:23].[CH2:27]([OH:29])[CH3:28]>>[C:2]1([C:8]2[O:9][C:10]3[C:18]([CH2:19][C:20]([O:29][CH2:27][CH3:28])=[O:23])=[CH:17][CH:16]=[CH:15][C:11]=3[C:12](=[O:14])[CH:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 146504442-(1-Bromocyclohexyl)-8-cyanomethyl-4-oxo-4H-[1]-benzopyran

Product 1

HCID 14650456HCID 14650456, compoundYield 56%

Procedure

2-(1-Bromocyclohexyl)-8-cyanomethyl-4-oxo-4H-[1]-benzopyran (5.0 g) and 50% sulfuric acid (4 ml) were added to ethanol (400 ml) and the mixture was refluxed for 8 hours. Then, ethanol (about 300 ml) was distilled off under reduced pressure and the residue was added to water. The mixture was extracted with ethyl acetate and the extract was washed with water, dried (MgSO4) and concentrated. The residue was recrystallized from ethyl acetate to obtain the title compound, yield 56%.

Workup

  1. temperaturethe mixture was refluxed for 8 hours
  2. distillationThen, ethanol (about 300 ml) was distilled off under reduced pressure
  3. additionthe residue was added to water
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe extract was washed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-91715fe907ea4772961b884df4ebe04a
Source dataset
uspto-grants-1990_02
Patent number
US04904690

Reaction notes

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