Toluene → HCID 20187900, compound

HRID 2308826Notes

Reaction equation

HRID 2308826 reaction equation
[Na].[CH3:2][C:3]([OH:9])([CH3:8])[CH:4]([OH:7])[CH2:5][OH:6].[C:10]1([CH3:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)C>[CH2:16]([O:6][CH2:5][CH:4]([O:7][CH2:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]([CH3:8])([OH:9])[CH3:2])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:16]([O:6][CH2:5][CH:4]([OH:7])[C:3]([CH3:8])([OH:9])[CH3:2])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 1140Toluene2×HCID 5360545SodiumHCID 130445963-Methylbutane-1,2,3-triol

Product 2

HCID 20187900HCID 20187900, compoundHCID 20187911HCID 20187911, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.460 g of sodium in 10 ml of ethanol is treated with 2.4 g of (RS)-3-methyl-1,2,3-butanetriol. 20 ml of toluene are added thereto and, with the simultaneous dropwise addition of 60 ml of toluene, solvent is distilled off slowly until the distillate amounts to 75 ml. The residual suspension is suction filtered, the residue is washed with ether and dried at room temperature/11 Torr. The salt is suspended in 10 ml of tetrahydrofuran, then 0.740 g of tetrabutylammonium iodide and 4.0 ml of benzyl bromide are added and the mixture is stirred at room temperature for 3 days. The mixture is diluted with benzene and concentrated at 30°/11 Torr. The residue is chromatographed on 30 g of silica gel with hexane/ether (4:1). There are thus obtained, besides 0.616 g of (RS)-1,2-dibenzyloxy-3-methyl-3-butanol, as the polar fraction 1.15 g of the desired product as a colourless oil of boiling point 150°/2 Torr (bulb-tube).

Workup

  1. distillationis distilled off slowly until the distillate amounts to 75 ml
  2. filtrationsuction filtered
  3. washthe residue is washed with ether
  4. customdried at room temperature/11 Torr
  5. addition0.740 g of tetrabutylammonium iodide and 4.0 ml of benzyl bromide are added
  6. additionThe mixture is diluted with benzene
  7. concentrationconcentrated at 30°/11 Torr
  8. customThe residue is chromatographed on 30 g of silica gel with hexane/ether (4:1)

Sources & evidence

ORD record
ord-259d634c2bd14586bf41bbee12762488
Source dataset
uspto-grants-1987_09
Patent number
US04691032

Reaction notes

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