4-Tert-octylphenol → HCID 18533585, compound

HRID 566169Notes

Reaction equation

HRID 566169 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:3])[CH3:2].[F:16][C:17]([O:22][CH2:23][CH:24]1[O:26][CH2:25]1)([F:21])[CH:18]([F:20])[F:19]>>[F:16][C:17]([F:21])([O:22][CH2:23][CH:24]([OH:26])[CH2:25][O:15][C:12]1[CH:11]=[CH:10][C:9]([C:1]([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:2])[CH3:3])=[CH:14][CH:13]=1)[CH:18]([F:19])[F:20]

Participants

3

Reactant 2

HCID 88144-Tert-octylphenolHCID 2776649(2H-Perfluoroethoxy)methyloxirane

Product 1

HCID 18533585HCID 18533585, compoundYield 108%

Conditions

Temperature
100 °C

Procedure

A 250 mL 2-neck flask was charged with 20.6 g (0.10 mol) of 4-tert-octylphenol obtained from Aldrich Chemical Co., a catalytic amount of dry, ground potassium carbonate obtained from EM Science, Inc. (1.38 g, 0.010 mol), a stir bar, and 95% ethanol (75 mL) under argon. The side arm was then stoppered with a rubber septum, and a condenser with an argon inlet was attached to the center neck. The system was evacuated and backflushed with argon three times. Stirring was commenced to dissolve the phenol, then glycidyl 1,1,2,2-tetrafluoroethyl ether (27.0 mL, 19.15 g, 0.11 mol) obtained from Aldrich Chemical Co., was added through the septum in two portions using a 20 mL glass syringe. The reaction was monitored by thin layer chromatography (TLC) while it refluxed for 24 hours in an oil bath at 100° C. The mixture was then allowed to cool and the ethanol removed by rotary evaporation. The product was obtained by dissolving the reaction mixture in 100 mL hexanes and extracting with 1×50 mL 5% NaOH in 15:85 v/v water/methanol followed by 2×50 mL deionized water washes. The methanol-water layers were back-extracted with 50 mL hexanes. After drying over anhydrous MgSO4, the combined hexanes were evaporated off to give 41.0 g (108% yield) of a pale yellow oil. The product was purified by fractional distillation under vacuum with 31.96 g (84%) of spectroscopically pure product being collected at 145-153° C. (0.2 mm Hg). The structure and purity of the compound were corroborated by proton (1H) and carbon-13 NMR spectrometry.

Workup

  1. custom, a catalytic amount of dry
  2. customThe side arm was then stoppered with a rubber septum, and a condenser with an argon inlet
  3. customThe system was evacuated
  4. dissolutionto dissolve the phenol
  5. addition, was added through the septum in two portions
  6. temperatureto cool
  7. customthe ethanol removed by rotary evaporation
  8. customThe product was obtained
  9. extractionextracting with 1×50 mL 5% NaOH in 15:85 v/v water/methanol
  10. extractionThe methanol-water layers were back-extracted with 50 mL hexanes
  11. dry with materialAfter drying over anhydrous MgSO4
  12. customthe combined hexanes were evaporated off

Sources & evidence

ORD record
ord-29c4127aa6354063b3a3e73dce3a6363
Source dataset
uspto-grants-2001_01
Patent number
US06174503B1

Reaction notes

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