Acetone → HCID 86744937, compound

HRID 1087392Notes

Reaction equation

HRID 1087392 reaction equation
[CH2:1]([OH:7])[C@H:2]([OH:6])[CH2:3][CH2:4][OH:5].C(=O)(O)[O-].[Na+].[CH3:13][C:14]([CH3:16])=O>Cl(O)(=O)(=O)=O.O>[C:14](=[C:1]([OH:7])[C@H:2]([OH:6])[CH2:3][CH2:4][OH:5])([CH3:16])[CH3:13]

Participants

6

Reactant 3

HCID 180AcetoneHCID 516892Sodium BicarbonateHCID 69942791,2,4-Butanetriol, (2R)-

Product 1

HCID 86744937HCID 86744937, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 24247Perchloric AcidCatalystHCID 962WaterSolvent

Procedure

(R)-(+)-1,2,4-Butanetriol (0.7 g, 6.6 mmol), prepared as described in step a) above, was stirred for 1.5 h in acetone (50 ml) containing 3 drops of conc. perchloric acid, a satured solution of sodium bicarbonate in water (5 ml) was added and the stirring was continued for additional 10 min. The precipitate was filtered off and the filtrate evaporated under reduced pressure (2.7 kPa, 30° C.). The residue was taken up in ethyl acetate, washed with saturated aqueous sodium bicarbonate (5 ml) and brine (5 ml), and dried over magnesium sulphate. Evaporation of the solvent and distillation gave the title compound as a colourless oil (0.3 g, 2.05 mmol, 31%): b.p. 104°-106° C. at~2.7 kPa. nD20 =1.4390.

Workup

  1. filtrationThe precipitate was filtered off
  2. customthe filtrate evaporated under reduced pressure (2.7 kPa, 30° C.)
  3. washwashed with saturated aqueous sodium bicarbonate (5 ml) and brine (5 ml)
  4. dry with materialdried over magnesium sulphate
  5. customEvaporation of the solvent and distillation

Sources & evidence

ORD record
ord-95dc4a34650b47ee84da867cb13429a5
Source dataset
uspto-grants-1991_07
Patent number
US05036071

Reaction notes

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