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Hydrochloric Acid → 1,1-Bis(4-hydroxyphenyl)-2,2-dichloroethylene

HRID 990301
Notes
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Reaction equation

HRID 990301 reaction equation
[OH-].[K+].[Cl:3][C:4]([Cl:24])=[C:5]([C:15]1[CH:20]=[CH:19][C:18]([O:21]C#N)=[CH:17][CH:16]=1)[C:6]1[CH:11]=[CH:10][C:9]([O:12]C#N)=[CH:8][CH:7]=1.ClC(Cl)(Cl)C(C1C=CC(O)=CC=1)C1C=CC(O)=CC=1.Cl>O.CO>[Cl:3][C:4]([Cl:24])=[C:5]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)[C:6]1[CH:7]=[CH:8][C:9]([OH:12])=[CH:10][CH:11]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 763021,1,1-Trichloro-2,2-bis(4-hydroxyphenyl)ethaneHCID 112212271,1-Dichloro-2,2-bis(4-cyanatophenyl)ethylene

Product 1

HCID 846771,1-Bis(4-hydroxyphenyl)-2,2-dichloroethylene

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A 4-necked 5-liter flask, equipped with a mechanical stirrer, a thermometer, and a condenser, is charged with methanol (800 g). Potassium hydroxide (440 g) is added in portions to the methanol solution. After the addition, the solution is cooled to 20° C. To this stirring solution, 1,1,1-trichloro-2,2-bis(4-hydroxyphenyl)ethane (420 g) is added in portions. The reaction temperature is kept below 40° C. After the addition, the temperature is raised to 50° C. and maintained for 2.5 hours. The reaction mixture is cooled to 20° C. and neutralized with 25% HCl solution. After the neutralization, the mixture is heated to reflux and water (480 g) is added. The mixture is allowed to cool to the room temperature. The precipitates are filtered and dried to afford 1,1-dichloro-2,2-bis(4-hydroxyphenyl)ethene as white solids with slight tan color.

Workup

  1. customA 4-necked 5-liter flask, equipped with a mechanical stirrer
  2. additionAfter the addition
  3. customis kept below 40° C
  4. additionAfter the addition
  5. temperaturethe temperature is raised to 50° C.
  6. temperaturemaintained for 2.5 hours
  7. temperatureAfter the neutralization, the mixture is heated
  8. temperatureto reflux
  9. temperatureto cool to the room temperature
  10. filtrationThe precipitates are filtered
  11. customdried

Sources & evidence

ORD record
ord-8539d6fe77a14cb59100a08c2748cce0
Source dataset
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06458993B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes