Dichloromethane → HCID 13064229, compound

HRID 894226Notes

Reaction equation

HRID 894226 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].Cl[CH2:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([CH2:19]Cl)[C:13]=1[OH:21].[Cl-].[Al+3].[Cl-].[Cl-].ClCCl>[N+](C1C=CC=CC=1)([O-])=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:9])=[C:7]([CH:8]=1)[CH2:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([CH2:19][C:5]2[CH:4]=[C:3]([C:1]#[N:2])[CH:8]=[CH:7][C:6]=2[OH:9])[C:13]=1[OH:21])#[N:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 130194-CyanophenolHCID 6451240Aluminum(III) ChlorideHCID 211628322,6-Bis(chloromethyl)-4-fluorophenol

Product 1

HCID 13064229HCID 13064229, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Procedure

p-Cyanophenol (19.4 g) and 2,6-bis(chloromethyl)-4-fluorophenol (17.0 g) were dissolved in nitrobenzene (250 ml) at 20°. The solution was cooled to 10° and crushed aluminium chloride (anhydrous 65 g) was added in 5 g portions over two hours. During the addition the temperature was maintained at 10°-12°. Stirring was continued at 20° for 14 hrs. The viscous black mixture was poured onto a vigorously stirred mixture of ice (2 l) and dichloro methane (2 l). The organic solvent layer was dried, dichloro methane and nitrobenzene removed by vacuum distillation and the residual tar passed through a silica column. The product, 2,6-bis(5-cyano-2-hydroxybenzyl)-4-fluorophenol (mp 222°) was obtained in 3% yield.

Workup

  1. temperatureThe solution was cooled to 10°
  2. additionwas added in 5 g portions over two hours
  3. additionDuring the addition the temperature
  4. temperaturewas maintained at 10°-12°
  5. customThe organic solvent layer was dried
  6. customdichloro methane and nitrobenzene removed by vacuum distillation

Sources & evidence

ORD record
ord-4112cdcdabda4ece86850fe58305beb4
Source dataset
uspto-grants-1981_08
Patent number
US04282390

Reaction notes

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