Dichloromethane → HCID 67053683, compound

HRID 1483880Notes

Reaction equation

HRID 1483880 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([C:9]2([C:22]3[CH:27]=[CH:26][CH:25]=[C:24](CO)[CH:23]=3)[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:15]3[C:10]2=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:6]=[CH:7][CH:8]=1.S(Cl)([Cl:32])=O.[CH2:34]([Cl:36])Cl>>[Cl:32][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH2:34][Cl:36])[CH:23]=3)[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:15]3[C:10]2=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 24386Thionyl ChlorideHCID 67053689HCID 67053689, compound

Product 1

HCID 67053683HCID 67053683, compound

Procedure

20.0 g (52.9 mmol) of 9,9-bis-(3-hydroxymethylphenyl)-9H-fluorene are dissolved in 300 ml of DCM. A mixture of 16.0 ml of thionyl chloride in 100 ml of dichloromethane is added dropwise to the solution, and the mixture is subsequently stirred at room temperature until the evolution of gas is complete. The solution is washed three times with 200 ml of sat. sodium hydrogencarbonate solution each time and twice with 200 ml of water each time and then dried over magnesium sulfate. The oily residue obtained after removal of the solvent in vacuo is recrystallised twice from ethanol with addition of a little acetone. Yield: 16.0 g (38.5 mmol), 72.8%, about 97% pure according to 1H-NMR.

Workup

  1. additionis added dropwise to the solution
  2. washThe solution is washed three times with 200 ml of sat. sodium hydrogencarbonate solution each time
  3. dry with materialtwice with 200 ml of water each time and then dried over magnesium sulfate
  4. customThe oily residue obtained
  5. customafter removal of the solvent in vacuo
  6. customis recrystallised twice from ethanol with addition of a little acetone

Sources & evidence

ORD record
ord-08f60b6f8c8343c0b2e782ebefdcbd7c
Source dataset
uspto-grants-2016_08
Patent number
US09416310B2

Reaction notes

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