Hexane → alpha-Tocopherol

HRID 975758Notes

Reaction equation

HRID 975758 reaction equation
[CH3:1][C:2]1[C:3]([OH:11])=[C:4]([CH3:10])[C:5]([CH3:9])=[C:6]([CH:8]=1)O.[CH3:12][CH:13]([CH2:15][CH2:16][CH2:17][CH:18]([CH2:20][CH2:21][CH2:22][CH:23]([CH2:25][CH2:26][CH2:27][C:28]([OH:32])([CH:30]=[CH2:31])[CH3:29])[CH3:24])[CH3:19])[CH3:14].CCCCCC>C1(C)C=CC=CC=1>[CH3:10][C:4]1[C:3]([OH:11])=[C:2]([CH3:1])[C:8]2[CH2:31][CH2:30][C@:28]([CH2:27][CH2:26][CH2:25][C@@H:23]([CH2:22][CH2:21][CH2:20][C@@H:18]([CH2:17][CH2:16][CH2:15][CH:13]([CH3:12])[CH3:14])[CH3:19])[CH3:24])([CH3:29])[O:32][C:6]=2[C:5]=1[CH3:9]

Participants

5

Reactant 3

HCID 8058HexaneHCID 10453Isophytol2×HCID 12785Trimethylhydroquinone2×

Product 1

HCID 14985alpha-TocopherolYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Suspended in 1 ml of toluene were 200 mg (1.316 mmol) of trimethylhydroquinone (TMH) and 100 mg of Sc-Bent, followed by heating under reflux for 10 minutes under an argon gas stream. After a solution of 430 mg (1.45 mmol) of isophytol in 1 ml of toluene was added dropwise over 5 minutes under heating and reflux, TMH and isophytol were further reacted each other for 1 hour. The reaction liquid was cooled, to which 20 ml of n-hexane were added. The resulting mixture was filtered and then concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column (eluent: n-hexane-ether system), whereby 527 mg of the title compound were obtained in the form of a brown oil. (Yield: 93%, GLC purity: 99%)

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 10 minutes under an argon gas stream
  3. temperatureunder heating
  4. temperaturereflux
  5. customThe reaction liquid
  6. additionwere added
  7. filtrationThe resulting mixture was filtered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by chromatography on a silica gel column (eluent: n-hexane-ether system)

Sources & evidence

ORD record
ord-7ebfe6d6957a45af92f52c772b7c8b1b
Source dataset
uspto-grants-1997_03
Patent number
US05610113

Reaction notes

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