1,2,6-Hexanetriol → 1,3-Dioxolane-4-butanol, 2-phenyl-

HRID 1712867

Reaction equation

HRID 1712867 reaction equation
[OH:1][CH2:2][CH:3]([OH:9])[CH2:4][CH2:5][CH2:6][CH2:7][OH:8].CO[CH:12](OC)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C=O)C.C(OCC)(=O)C>[C:13]1([CH:12]2[O:9][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][OH:8])[CH2:2][O:1]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 78231,2,6-HexanetriolHCID 62375Benzaldehyde dimethyl acetal

Product 1

HCID 2366801,3-Dioxolane-4-butanol, 2-phenyl-Yield 66.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1,2,6-trihydroxyhexane (10.0 g, 74.6 mmol) and benzaldehyde dimethylacetal (15.0 g, 98.7 mmol) in dry DMF (10 mL) was added Amberlyst 15 (5.0 g). The mixture was stirred at 100° C. for 5 min, then cooled and filtered. The filtrate was concentrated and residue obtained was re-dissolved in ethyl acetate. After being washed with water and brine, the solution was dried over Na2SO4. The crude product obtained after evaporation of the solvent was chromatographed on silica eluting with ethyl acetate. Concentration of the proper fractions afforded 11.0 g (66%) of the title product (a mixture of diastereomers) as a colorless oil: 1H NMR (CDCl3, 300 MHz, ppm) 7.48 (m, 2H), 7.39 (m, 3H), 5.92 (s, 0.4H), 5.80 (s, 0.6H), 4.3-4.1 (m, 2H), 3.64 (m, 3H), 1.8-1.4 (m, 6H).

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customresidue obtained
  5. washAfter being washed with water and brine
  6. dry with materialthe solution was dried over Na2SO4
  7. customThe crude product obtained
  8. customafter evaporation of the solvent
  9. customwas chromatographed on silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-0b25aef54a424adc97b094ccbfed1b17
Source dataset
uspto-grants-2010_09
Patent number
US07794945B2

Linked notes

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