Hydrochloric Acid → HCID 14250430, compound

HRID 2414002Notes

Reaction equation

HRID 2414002 reaction equation
Cl.N[C:3]1[CH:4]=[C:5]([C:9](C2C=CC=C(N)C=2)([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])[CH:6]=[CH:7][CH:8]=1.N([O-])=[O:26].[Na+].[C:29]1([OH:35])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[OH:35][C:29]1[CH:34]=[C:33]([C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([OH:26])[CH:4]=2)([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])[CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 996PhenolHCID 6305662,2-Bis(3-aminophenyl)hexafluoropropaneHCID 23668193Sodium Nitrite

Product 1

HCID 14250430HCID 14250430, compound

Conditions

Temperature
80 °C

Procedure

To make the desired bisphenol from this diamine, we prepare a solution of 60 milliliters of concentrated hydrochloric acid, 200 milliliters of ice and 33.4 grams (0.1 mole) of 2,2-bis(3-aminophenyl)hexafluoropropane, and add thereto an aqueous solution of sodium nitrite (0.2 mole). We stir the mixture slowly, and heat to 80° C. for two hours. After the desired phenol separates, we extract it three times with 100 milliliters of ether each time, then wash the organic phase with water, sodium bicarbonate, and finally with saturated ammonium chloride. We then distill to obtain 33.6 grams of 2,2-bis(3-hydroxyphenyl)hexafluoropropane. From this bisphenol, we prepare the meta-substituted bisbenzenethiols of this invention following the same sequence of steps that produces the para-substituted bisbenzenethiols.

Workup

  1. additionadd
  2. extractionwe extract it three times with 100 milliliters of ether each time
  3. washwash the organic phase with water, sodium bicarbonate
  4. distillationWe then distill

Sources & evidence

ORD record
ord-47ae4291a0844a19880a2ac30ffc2a05
Source dataset
uspto-grants-1988_01
Patent number
US04720590

Reaction notes

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