HCID 11652005, compound → HCID 15149208, compound

HRID 326298Notes

Reaction equation

HRID 326298 reaction equation
C[O:2][C:3]1[C:8]2[C:9](=[O:18])[CH2:10][C:11]3([O:17][C:7]=2[CH:6]=[C:5]([O:19]C)[CH:4]=1)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3>Br>[OH:2][C:3]1[C:8]2[C:9](=[O:18])[CH2:10][C:11]3([O:17][C:7]=2[CH:6]=[C:5]([OH:19])[CH:4]=1)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3

Participants

3

Reactant 1

HCID 11652005HCID 11652005, compound

Product 1

HCID 15149208HCID 15149208, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A mixture of 5,7-dimethoxyspiro[2H-1-benzopyran-2,1'-cyclohexan]-4(3H)-one [H.F.Birch, A.Robertson, and T.S.Subramanjam, J.Chem.Soc., 1832 (1936)] (1.3 g, 6.25 mmol) and 48% hydrobromic acid (50 ml) is heated to reflux for one hour. After cooling, the reaction mixture is concentrated under reduced pressure. The concentrate is extracted with diethyl ether and the extract is washed with water, dried, and concentrated. The residue is placed on a silica gel column and eluted with diethyl ether. The eluate is treated with ether to yield the title compound as a crystalline solid (0.65 g, 58%).

Workup

  1. temperatureis heated
  2. temperatureto reflux for one hour
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture is concentrated under reduced pressure
  5. extractionThe concentrate is extracted with diethyl ether
  6. washthe extract is washed with water
  7. customdried
  8. concentrationconcentrated
  9. washeluted with diethyl ether
  10. additionThe eluate is treated with ether

Sources & evidence

ORD record
ord-f93d94d6068f49aebfc9b21074ddd4b4
Source dataset
uspto-grants-1993_12
Patent number
US05268386

Reaction notes

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