3,4-Dichlorobenzotrifluoride → HCID 13094093, compound

HRID 1834355Notes

Reaction equation

HRID 1834355 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][C:7]=1Cl.[K].C1(C(C2[C:27]([CH2:28][O:29][CH2:30][C:31]3[C:36](C4C(=CC=C(O)C=4)O)=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:26][CH:25]=[CH:24][CH:23]=2)=CC(=CC=1)O)O.[OH-:45].[K+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][C:7]=1[O:45][C:25]1[CH:24]=[CH:23][C:28]([O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 94813,4-DichlorobenzotrifluorideHCID 14797Potassium HydroxideHCID 5462222PotassiumHCID 1317110222-[2-[[2-(2,5-Dihydroxyphenyl)phenyl]methoxymethyl]phenyl]benzene-1,4-diol

Product 1

HCID 13094093HCID 13094093, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
120 °C

Procedure

To as flask equipped with a stirrer, thermometer, condenser and drying tube are charged 3,4-dichlorobenzotrifluoride (43 g., 0.20 mole), potassium 4-benzyloxyphenate (47.5 g., 0.20 mole-prepared from hydroquinone monobenzylether using potassium hydroxide pellets dissolved in methanol and removal of the solvent in vacuo and subsequent precipitation in ether) and dimethyl sulfoxide (400 ml.). The reaction mixture is then warmed to 120° C and maintained at 135° C for 3 hours, cooled, poured into water (3 liters) and extracted into hexane (500 ml., then 300 ml., then 200 ml.) and the combined hexane extracts washed again with water (200 ml.), dried with anhydrous magnesium sulfate, and the solvent removed in vacuo to give 52.6 g. (70% yield) of 4-benzyloxyphenyl 2-chloro-4trifluoromethylphenyl ether, mp 63°-6° C, which is recrystallized from methanol to give white crystals, mp 69°-71° C.

Workup

  1. customTo as flask equipped with a stirrer
  2. customthermometer, condenser and drying tube
  3. customremoval of the solvent
  4. customin vacuo and subsequent precipitation in ether) and dimethyl sulfoxide (400 ml.)
  5. temperaturemaintained at 135° C for 3 hours
  6. temperaturecooled
  7. additionpoured into water (3 liters)
  8. extractionextracted into hexane (500 ml
  9. wash) and the combined hexane extracts washed again with water (200 ml.)
  10. dry with materialdried with anhydrous magnesium sulfate
  11. customthe solvent removed in vacuo
  12. customto give 52.6 g

Sources & evidence

ORD record
ord-e1f0713d1c8e4d0c885584fecb75f132
Source dataset
uspto-grants-1978_01
Patent number
US04070178

Reaction notes

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