Hexamethylphosphoramide → 2,6-Dichlorophenol

HRID 1703363Notes

Reaction equation

HRID 1703363 reaction equation
[Cl:1][C:2]1(Cl)[CH2:7][CH2:6][CH2:5][C:4](Cl)([Cl:8])[C:3]1=[O:10].CN(P(N(C)C)(N(C)C)=O)C>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[OH:10]

Participants

3

Reactant 2

HCID 12679HexamethylphosphoramideHCID 774072,2,6,6-Tetrachlorocyclohexan-1-one

Product 1

HCID 68992,6-DichlorophenolYield 63.8%

Procedure

118 g (0.5 mol) of 2,2,6,6-tetrachlorocyclohexanone and 1 g (0.006 mol) of hexamethylphosphorotriamide were introduced into the reactor used in Example 1. The reaction mixture was heated at 150°-180° C., under stirring; the reaction was terminated when the evolution of hydrogen chloride from the reaction mixture ceased. The reaction mixture was then distilled under reduced pressure (boiling point (20 mm Hg)=100° C.) to yield 52 g of 2,6-dichlorophenol.

Workup

  1. temperatureThe reaction mixture was heated at 150°-180° C.
  2. customthe reaction was terminated when the evolution of hydrogen chloride from the reaction mixture
  3. distillationThe reaction mixture was then distilled under reduced pressure (boiling point (20 mm Hg)=100° C.)

Sources & evidence

ORD record
ord-a1ac4ad257fb463f919bfb755b550c04
Source dataset
uspto-grants-1982_09
Patent number
US04351969

Reaction notes

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