Trifluoroacetic acid → Phytyltrimethylhydroquinone

HRID 1865403Notes

Reaction equation

HRID 1865403 reaction equation
[CH3:1][C:2]1[C:3]([OH:11])=[C:4]([CH3:10])[C:5]([CH3:9])=[C:6]([CH:8]=1)[OH:7].[C:12]1(=O)OC(C)CO1.FC(F)(F)C(O)=O.[CH3:26][CH:27]([CH2:29][CH2:30][CH2:31][CH:32]([CH2:34][CH2:35][CH2:36][CH:37]([CH2:39][CH2:40][CH2:41][C:42](O)([CH:44]=C)[CH3:43])[CH3:38])[CH3:33])[CH3:28]>O.CCCCCCC>[CH2:1]([C:2]1[C:3]([OH:11])=[C:4]([CH3:10])[C:5]([CH3:9])=[C:6]([OH:7])[C:8]=1[CH3:12])/[CH:26]=[C:27](/[CH2:29][CH2:30][CH2:31][C@@H:32]([CH2:34][CH2:35][CH2:36][C@@H:37]([CH2:39][CH2:40][CH2:41][CH:42]([CH3:44])[CH3:43])[CH3:38])[CH3:33])\[CH3:28]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7924Propylene CarbonateHCID 10453IsophytolHCID 12785Trimethylhydroquinone

Product 1

HCID 87503419Phytyltrimethylhydroquinone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8900HeptaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of trimethylhydroquinone (15.5 g, 100 mmol), propylene carbonate (100 ml) and heptane (100 ml) was heated to 140° C. (bath temperature) in a three-necked reaction flask equipped with a water separator, a reflux condenser and argon gasification means. Trifluoroacetic acid (0.5 ml, 6.52 mmol) was then added dropwise using a syringe to the biphasic reaction mixture at reflux temperature, followed by isophytol (35.99 ml, 100 mmol) to the resulting solution over a period of 30 minutes at 140° C. (internal temperature 100° C.). After stirring for a further 10 minutes at 140° C., water and heptane were distilled off from the reaction mixture. The produced phytyltrimethylhydroquinone was extracted with three 50 ml portions of heptane from the carbonate phase, and the combined heptane phase was cooled down to room temperature. The resulting yellowish suspension was filtered through a P4 frit (requiring 2-3 days) and washed with 100 ml of cold propylene carbonate (4° C.) and 500 ml of cold heptane (4° C.) to remove traces of trimethylhydroquinone and by-products. The white waxy residue was dried for 3 hours under high vacuum. The so produced phytyltrimethylhydroquinone was found to have a purity of about 95%.

Workup

  1. customto the biphasic reaction mixture
  2. temperatureat reflux temperature
  3. custom(internal temperature 100° C.)
  4. distillationwater and heptane were distilled off from the reaction mixture
  5. extractionThe produced phytyltrimethylhydroquinone was extracted with three 50 ml portions of heptane from the carbonate phase
  6. temperaturethe combined heptane phase was cooled down to room temperature
  7. filtrationThe resulting yellowish suspension was filtered through a P4 frit (requiring 2-3 days)
  8. washwashed with 100 ml of cold propylene carbonate (4° C.) and 500 ml of cold heptane (4° C.)
  9. customto remove traces of trimethylhydroquinone and by-products
  10. customThe white waxy residue was dried for 3 hours under high vacuum

Sources & evidence

ORD record
ord-fc97878bb7b84c39822c09c260b4b5dd
Source dataset
uspto-grants-2009_12
Patent number
US07626046B2

Reaction notes

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