Phenol → 1,1,1-Trichloro-2,2-bis(4-hydroxyphenyl)ethane

HRID 840332

Reaction equation

HRID 840332 reaction equation
S(=O)(=O)(O)O.[C:6]1([OH:12])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O=[CH:14][C:15]([Cl:18])([Cl:17])[Cl:16]>O>[Cl:16][C:15]([Cl:18])([Cl:17])[CH:14]([C:9]1[CH:10]=[CH:11][C:6]([OH:12])=[CH:7][CH:8]=1)[C:9]1[CH:10]=[CH:11][C:6]([OH:12])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 1118Sulfuric Acid2×HCID 6407Chloral

Product 1

HCID 763021,1,1-Trichloro-2,2-bis(4-hydroxyphenyl)ethaneYield 98.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 4-necked 3-L flask, equipped with a mechanical stirrer, a nitrogen inlet, and thermometer, is charged with 83% sulfuric acid (640 g). To this sulfuric acid, phenol (354 g) is added at 20° C. Chloral (200 g) in an additional funnel is added dropwise to the phenolic stirring mixture. The reaction temperature is maintained below 30° C. After the addition, the mixture is allowed to stir at room temperature for 18 hours, before water (640 g) is added. The resulting mixture is filtered and washed with more water to afford 1,1,1-trichloro-2,2-bis(4-hydroxyphenyl)ethane (423 g) as white solids.

Workup

  1. customA 4-necked 3-L flask, equipped with a mechanical stirrer, a nitrogen inlet
  2. temperatureThe reaction temperature is maintained below 30° C
  3. additionAfter the addition
  4. additionis added
  5. filtrationThe resulting mixture is filtered
  6. washwashed with more water

Sources & evidence

ORD record
ord-400d79d45a384523bd918e99381092e8
Source dataset
uspto-grants-2002_04
Patent number
US06365671B1

Linked notes

Loading…