Acetone → HCID 19756577, compound

HRID 1587812Notes

Reaction equation

HRID 1587812 reaction equation
[CH3:1][O:2][CH:3](OC)[C:4]([OH:24])([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH:7]=1)[CH3:5].C(=O)(O)[O-].[Na+].[CH3:32][C:33]([CH3:35])=[O:34]>S(=O)(=O)(O)O>[CH3:32][C:33]1([CH3:35])[O:24][C:4]([CH3:5])([C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:15]=3)[CH:7]=2)[CH:3]([O:2][CH3:1])[O:34]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 516892Sodium BicarbonateHCID 19756580HCID 19756580, compound

Product 1

HCID 19756577HCID 19756577, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

Concentrated sulphuric acid (5 drops) was added to a solution of 2-hydroxy-2-[3-(naphth-2-ylmethoxy)phenyl]propionaldehyde dimethyl acetal (1.5 g) in acetone (30 ml) and the mixture was stirred at ambient temperature for 5 hours. A saturated aqueous sodium bicarbonate solution (30 ml) was added and the bulk of the acetone was evaporated. The residue was partitioned between diethyl ether and water. The organic phase was washed with water and with a saturated sodium chloride solution, dried (MgSO4) and evaporated. The residue, comprising a mixture of diastereoisomers, was purified by column chromatography using increasingly polar mixtures of petroleum ether (b.p. 40°-60° C.) and methylene chloride as eluent. There was thus obtained the less polar diastereoisomer, (4SR,5RS)-2,2,4-trimethyl-5-methoxy-4-[3-(naphth-2-ylmethoxy)phenyl]-1,3-dioxolane (0.39 g, 31%), m.p. 100°-103° C.; the 4-methyl and 5-methoxy groups being in a cis-relationship.

Workup

  1. customthe bulk of the acetone was evaporated
  2. customThe residue was partitioned between diethyl ether and water
  3. washThe organic phase was washed with water and with a saturated sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. additiona mixture of diastereoisomers
  7. customwas purified by column chromatography
  8. temperatureusing increasingly polar mixtures of petroleum ether (b.p. 40°-60° C.) and methylene chloride as eluent

Sources & evidence

ORD record
ord-8e14e081c7e349739a538293e71bf003
Source dataset
uspto-grants-1993_06
Patent number
US05219881

Reaction notes

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