Benzaldehyde dimethyl acetal → 2-Phenyl-1,3-oxathiolane

HRID 2251409Notes

Reaction equation

HRID 2251409 reaction equation
CO[CH:3]([O:10][CH3:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[SH:12][CH2:13]CCO>C1COCC1.O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3]>[C:4]1([CH:3]2[S:12][CH2:13][CH2:11][O:10]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 62375Benzaldehyde dimethyl acetalHCID 882113-Mercaptopropanol

Product 1

HCID 977972-Phenyl-1,3-oxathiolaneYield 105.8%

Reagents, catalysts & solvents 2

HCID 71586775BentoniteCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To an oven-dried 250 mL flask fitted with a magnetic stirring bar and reflux condenser was introduced 0.4 g of Montmorillonite KSF, 1.65 g (10.8 mmol) of benzaldehyde dimethyl acetal in 35 mL of THF, followed by 1.0 g (10.8 mmol) of 3-mecapto-1-propanol in 5 mL of THF. The mixture was refluxed under nitrogen for 12 hours. After cooling to room temperature and filtered, the filtrate was washed with saturated NaHCO3 (2×20 mL), saturated NaCl (20 mL) and dried over MgSO4 (anhydrous). The solvent was evaporated; a chromatograph using silica gel [elution with Hexane/Et2O (70/30)] was obtained on the residue, yielding 1.9 g (97%) of 2-phenyl-1,3-oxathiolane. 1H-NMR (CDCl3): δ 1.74 (m, 1 H), 2.11 (m, 1H), 2.82, (m, 1H), 3.22 (m, 1H), 3.81 (m, 1H), 4.35 (m, 1H), 5.80 (s, 1H), 7.36 (m, 3H), 7.49 (m, 2H). 13C-NMR (CDCl3): δ 25.73, 29.26, 70.74, 126.19, 128.46, 128.53, 139.52.

Workup

  1. customTo an oven-dried 250 mL flask fitted with a magnetic stirring bar
  2. temperaturereflux condenser
  3. temperatureThe mixture was refluxed under nitrogen for 12 hours
  4. filtrationfiltered
  5. washthe filtrate was washed with saturated NaHCO3 (2×20 mL), saturated NaCl (20 mL)
  6. dry with materialdried over MgSO4 (anhydrous)
  7. customThe solvent was evaporated
  8. customwas obtained on the residue

Sources & evidence

ORD record
ord-0b861dfac167450489112ca63b81b770
Source dataset
uspto-grants-2008_01
Patent number
US07319123B2

Reaction notes

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