Sulfuric Acid → 2,4-Bis(trichloromethyl)-2H,4H-1,3-benzodioxin-6-ol

HRID 224399Notes

Reaction equation

HRID 224399 reaction equation
[Cl-].[Cl:2][C:3]([Cl:21])([Cl:20])[CH:4]1[O:9][CH:8]([C:10]([Cl:13])([Cl:12])[Cl:11])[C:7]2[CH:14]=[C:15]([N+]#N)[CH:16]=[CH:17][C:6]=2[O:5]1.S(=O)(=O)(O)[OH:23]>O>[OH:23][C:15]1[CH:16]=[CH:17][C:6]2[O:5][CH:4]([C:3]([Cl:21])([Cl:20])[Cl:2])[O:9][CH:8]([C:10]([Cl:13])([Cl:12])[Cl:11])[C:7]=2[CH:14]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 233329382,4-Bis(trichloromethyl)-2H,4H-1,3-benzodioxine-6-diazonium chloride

Product 1

HCID 233329442,4-Bis(trichloromethyl)-2H,4H-1,3-benzodioxin-6-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 2,4-bis(trichloromethyl)benzo[1,3]dioxin-6-diazonium chloride (5 g.) concentrated sulphuric acid (125 ml.) and water (125 ml.) was stirred and heated at 160° C. for 20 minutes. The reaction mixture was cooled to ambient temperature and the product was filtered off, washed with water, and crystallised from cyclohexane, to give 6-hydroxy-2,4-bis(trichloromethyl)benzo[1,3]dioxin, m.p. 167°-169° C.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. filtrationthe product was filtered off
  3. washwashed with water
  4. customcrystallised from cyclohexane

Sources & evidence

ORD record
ord-2e6d2e1a242c4bfba1b78b056106ce8a
Source dataset
uspto-grants-1980_11
Patent number
US04232032

Reaction notes

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