Hydrochloric Acid → alpha-Tocopherol

HRID 465733Notes

Reaction equation

HRID 465733 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[C:6]([CH3:9])[C:5]([CH3:10])=[C:4]([OH:11])[C:3]=1[CH3:12].[H-].[Na+].C([Li])CCC.O1[C:22]([CH3:39])([CH2:23][CH2:24][CH2:25][CH:26]([CH3:38])[CH2:27][CH2:28][CH2:29][CH:30]([CH3:37])[CH2:31][CH2:32][CH2:33][CH:34]([CH3:36])[CH3:35])[CH2:21]1.Cl>O1CCCC1>[CH3:12][C:3]1[C:4]([OH:11])=[C:5]([CH3:10])[C:6]2[CH2:9][CH2:36][C@:34]([CH2:33][CH2:32][CH2:31][C@@H:30]([CH2:29][CH2:28][CH2:27][C@@H:26]([CH2:25][CH2:24][CH2:23][CH:22]([CH3:39])[CH3:21])[CH3:38])[CH3:37])([CH3:35])[O:8][C:7]=2[C:2]=1[CH3:1]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 136346DurohydroquinoneHCID 128109942-Methyl-2-(4,8,12-trimethyltridecyl)oxiraneHCID 178418339Butyllithium

Product 1

HCID 14985alpha-TocopherolYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10 g (66.7 mmol) of tetramethylhydroquinone are dissolved in 100 ml of dry tetrahydrofuran, 4 g (139 mmol) of sodium hydride (80% in mineral oil) are added thereto at room temperature, 45 ml of butyllithium (1.6 molar in hexane) are subsequently added dropwise and the mixture is stirred for 1 hour. 10 g (44.3 mmol) of 1,2-epoxy -2,6,10,14-tetramethylpentadecane are now added dropwise; the mixture is left to react for 12 hours while stirring. 100 ml of 1N methanolic hydrochloric acid are added and the mixture is stirred at 50° C. for 2 hours. The mixture is subsequently concentrated at 50° C. and the residue is chromatographed on silica gel with toluene, whereby there are obtained 14.9 g (75%) of α-tocopherol.

Workup

  1. waitthe mixture is left
  2. customto react for 12 hours
  3. stirringwhile stirring
  4. stirringthe mixture is stirred at 50° C. for 2 hours
  5. concentrationThe mixture is subsequently concentrated at 50° C.
  6. customthe residue is chromatographed on silica gel with toluene, whereby there

Sources & evidence

ORD record
ord-1292dbe726424dd69ce7238e072606bc
Source dataset
uspto-grants-1992_10
Patent number
US05153344

Reaction notes

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