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

HRID 1957778Notes

Reaction equation

HRID 1957778 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.O.C1(C)C(S(O)(=O)=O)=CC=CC=1>>[OH:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:2][O:1][CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:9]1

Participants

4

Reactant 3

HCID 78231,2,6-HexanetriolHCID 62375Benzaldehyde dimethyl acetalHCID 124969952-Methylbenzenesulfonic acid hydrate

Product 1

HCID 2366801,3-Dioxolane-4-butanol, 2-phenyl-Yield 27.8%

Procedure

A mixture of 1,2,6-trihydroxyhexane (2.58 g) and benzaldehyde dimethyl acetal (3.18 g) is treated with toluene sulfonic acid hydrate (2.08 g). The mixture is allowed to stir at room temperature for 60 hours, and is then partitioned between saturated aqueous sodium bicarbonate (50 ml) and methylene chloride (20 ml). The benzaldehyde dimethyl acetal (3.18 g) is treated with toluene sulfonic acid hydrate (2.08 g). The mixture is allowed to stir at room temperature for 60 hours, and is then partitioned between saturated aqueous sodium bicarbonate (50 ml) and methylene chloride (20 ml). The layers are separated, the aqueous layer is re-extracted with methylene chloride, the organic layers are dried over anhydrous sodium sulfate, filtered, and concentrated to an oil (2.66 g), which is purified by column chromatography (silica gel, 1:1 ethyl acetate/hexanes). Pooling and concentrating the appropriate fractions give the title compound as an oil (1.19 g): TLC Rf =0.18 (silica, 1:1 ethyl acetate/hexanes); 1H NMR (CDCl3), δ, 1.62 (m, 6H), 3.67 (m, 3H), 3.25 (m, 2H), 6.37 (s, 0.6H), 6.50 (s, 0.4H), 8.04 (br. s, 5H).

Workup

  1. customis then partitioned between saturated aqueous sodium bicarbonate (50 ml) and methylene chloride (20 ml)
  2. additionThe benzaldehyde dimethyl acetal (3.18 g) is treated with toluene sulfonic acid hydrate (2.08 g)
  3. stirringto stir at room temperature for 60 hours
  4. customis then partitioned between saturated aqueous sodium bicarbonate (50 ml) and methylene chloride (20 ml)
  5. customThe layers are separated
  6. extractionthe aqueous layer is re-extracted with methylene chloride
  7. dry with materialthe organic layers are dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to an oil (2.66 g), which
  10. customis purified by column chromatography (silica gel, 1:1 ethyl acetate/hexanes)
  11. concentrationPooling and concentrating the appropriate fractions

Sources & evidence

ORD record
ord-12390132c183406d8f12e77d827cedb4
Source dataset
uspto-grants-1998_07
Patent number
US05786512

Reaction notes

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