Phenol → HCID 19825286, compound

HRID 2198618Notes

Reaction equation

HRID 2198618 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][C:9](C1C=CC=CC=1O)([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[C:10]([F:13])([F:12])[F:11]>>[CH3:8][C:9]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)([C:4]1[CH:5]=[CH:6][C:1]([OH:7])=[CH:2][CH:3]=1)[C:10]([F:11])([F:12])[F:13]

Participants

3

Reactant 2

HCID 996PhenolHCID 20520002HCID 20520002, compound

Product 1

HCID 19825286HCID 19825286, compound

Procedure

Repeating the process of Example 5 using 470 g (5 moles) of phenol in place of the xylenol, yielded a reaction mixture consisting of 66% of 4,4-(1-methyltrifluoroethylidene)bisphenol and 34% of 2,4'-(1-methyltrifluoroethylidene)bisphenol. After the removal of excess phenol by distillation, the mixture of the two isomers was readily separated by elution chromatography over silica, using methylene chloride as eluant. After the emergence of the 2,4'-isomer, the 4,4'-isomer was eluted. The 4,4'-isomer crystallized out readily from the concentrated solution in the form of white crystals which melted at 93°-94.5° C. and had a purity of 98.2%.

Workup

  1. customyielded a reaction mixture
  2. customAfter the removal of excess phenol
  3. distillationby distillation
  4. additionthe mixture of the two isomers
  5. customwas readily separated by elution chromatography over silica
  6. washAfter the emergence of the 2,4'-isomer, the 4,4'-isomer was eluted
  7. customThe 4,4'-isomer crystallized out readily from the concentrated solution in the form of white crystals which melted at 93°-94.5° C.

Sources & evidence

ORD record
ord-ece8c6c2755c481b821608977fbbe4d5
Source dataset
uspto-grants-1982_11
Patent number
US04358624

Reaction notes

Loading…