Pentachlorophenol → HCID 21445183, compound

HRID 597482Notes

Reaction equation

HRID 597482 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[C:6]([Cl:9])[C:5]([Cl:10])=[C:4]([Cl:11])[C:3]=1[Cl:12].[C:13](=[O:16])([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:22][C:23]1([CH2:27]Cl)[CH2:26][O:25][CH2:24]1>O.CN(C)C=O>[Cl:1][C:2]1[C:7]([O:8][CH2:27][C:23]2([CH2:22][O:16][C:13]3[C:6]([Cl:9])=[C:5]([Cl:10])[C:4]([Cl:11])=[C:3]([Cl:12])[C:2]=3[Cl:1])[CH2:24][O:25][CH2:26]2)=[C:6]([Cl:9])[C:5]([Cl:10])=[C:4]([Cl:11])[C:3]=1[Cl:12]

Participants

7

Reactant 4

HCID 992PentachlorophenolHCID 4875Potassium IodideHCID 6550Oxetane, 3,3-bis(chloromethyl)-HCID 11430Potassium Carbonate

Product 1

HCID 21445183HCID 21445183, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

This reaction was carried out similarly to that described in Example 1. Pentachlorophenol (469 g., 1.86 moles), potassium carbonate (262 g., 1.9 moles), potassium iodide (4 g.) and 1.5 liters of dimethyl formamide were charged to a 3 liter reaction flask. The mixture was stirred and heated in a nitrogen atmosphere. When the temperature reached 95° C., 140 g. (0.9 moles) of 3,3-bischloromethyl oxetane was added. The reaction mixture was slowly heated to about 140° C. and held 3 hours. After cooling to 63° C., 700 ml. of water was added to the mixture. After standing overnight, the reaction mixture was filtered. The recovered crystalline 3,3-bis[pentachlorophenoxymethyl]oxetane was washed on the funnel with six portions of water, three portions of ethanol and three portions of 2-butanone. The yield of oven-dried, cream-colored crystals was 480 g. (87%). The compound melted at 229°-230° C. If desired, this compound can be recrystallized from dioxane.

Workup

  1. temperatureheated in a nitrogen atmosphere
  2. customreached 95° C.
  3. temperatureAfter cooling to 63° C.
  4. waitAfter standing overnight
  5. filtrationthe reaction mixture was filtered
  6. washThe recovered crystalline 3,3-bis[pentachlorophenoxymethyl]oxetane was washed on the funnel with six portions of water, three portions of ethanol and three portions of 2-butanone
  7. customThe yield of oven-dried
  8. customthis compound can be recrystallized from dioxane

Sources & evidence

ORD record
ord-d838a6c2a1664f99aad229bea729c165
Source dataset
uspto-grants-1977_03
Patent number
US04014855

Reaction notes

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