Benzyl Alcohol → 3-(Benzyloxy)propane-1,2-diol

HRID 1496906Notes

Reaction equation

HRID 1496906 reaction equation
[CH2:1]1[O:3][C@H:2]1[CH2:4][OH:5].[CH2:6]([OH:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[F-].[Cs+]>>[CH2:6]([O:13][CH2:1][C@@H:2]([OH:3])[CH2:4][OH:5])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 244Benzyl Alcohol2×HCID 25953Cesium fluorideHCID 6973630(-)-Glycidol

Product 1

HCID 69508413-(Benzyloxy)propane-1,2-diolYield 19.4%

Conditions

Temperature
120 °C

Procedure

A mixture of (S)-glycidol (77) (20 g, 0.27 mol), benzyl alcohol (27.9 mL, 0.27 mol) and CsF (0.82 g, 5.40 mmol) was heated with stirring at 120° C. for 16 h. Unreacted benzyl alcohol was removed using a rotary evaporator attached to a high vacuum line. The product was partitioned between EtOAc and water, and the organic extract was evaporated and chromatographed on silica. Elution with petroleum ether gave fore fractions, and then further elution with EtOAc/petroleum ether (3:7) gave (2S)-3-(benzyloxy)-1,2-propanediol (78) (9.52 g, 19%) as a viscous oil: [α]19 −3.64° (c, 6.59, CHCl3); 1H NMR (CDCl3) δ 7.38-7.28 (m, 5H), 4.56 (s, 2H), 3.92-3.87 (m, 1H), 3.71 (dd, J=11.4, 3.9 Hz, 1H), 3.64 (dd, J=11.4, 5.4 Hz, 1H), 3.61-3.57 (m, 2H), 2.60 (br, 1H), 2.22 (br, 1H). APCI MS m/z 183 [M+H]+.

Workup

  1. temperaturewas heated
  2. customwas removed
  3. customa rotary evaporator
  4. customThe product was partitioned between EtOAc and water
  5. extractionthe organic extract
  6. customwas evaporated
  7. customchromatographed on silica
  8. washElution with petroleum ether
  9. customgave fore fractions
  10. washfurther elution with EtOAc/petroleum ether (3:7)

Sources & evidence

ORD record
ord-8402e89fea5f4edab6896e4fd0af9ddc
Source dataset
uspto-grants-2015_12
Patent number
US09198913B2

Reaction notes

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