Water → HCID 15818603, compound

HRID 1720865Notes

Reaction equation

HRID 1720865 reaction equation
O[C:2]1([CH:17]=[CH2:18])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]1=2.S(Cl)([Cl:21])=O.O>ClCCl>[Cl:21][CH2:18][CH:17]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 15186376HCID 15186376, compound

Product 1

HCID 15818603HCID 15818603, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-hydroxy-5-vinyl-5H-dibenzo[a,d]cycloheptene (11 g, 48 mmol) in dichloromethane (300 ml) at 0° C. under argon atmosphere is added dropwise thionylchloride (62 mmol, 4.6 ml). The mixture is then stirred for 4 hours at room temperature. Water (100 ml) is added, the organic phase is removed and the aqueous phase is extracted with ether (350 ml). The combined organic phases are washed with water, saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is taken up in 150 ml of hot isooctane, the insoluble material is removed by decantation and the solution is cooled to room temperature, whereby the expected product crystallizes. The crystalline material is filtered, washed with isooctane and dried: 9 g of the pure title compound is obtained.

Workup

  1. customthe organic phase is removed
  2. extractionthe aqueous phase is extracted with ether (350 ml)
  3. washThe combined organic phases are washed with water, saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customthe insoluble material is removed by decantation
  8. temperaturethe solution is cooled to room temperature
  9. customwhereby the expected product crystallizes
  10. filtrationThe crystalline material is filtered
  11. washwashed with isooctane
  12. customdried

Sources & evidence

ORD record
ord-e57d27b6c08747ca884ea778f7380309
Source dataset
uspto-grants-1996_04
Patent number
US05508280

Reaction notes

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