Hydrochloric Acid → 2-[3-(4-Isopropoxyphenyl)propyl]-1,3-dioxolane

HRID 1739040Notes

Reaction equation

HRID 1739040 reaction equation
[H-].[Na+].[Br-].[O:4]1[CH2:8][CH2:7][O:6][CH:5]1[CH2:9][CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH:30]([O:33][C:34]1[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][CH:35]=1)([CH3:32])[CH3:31].Cl>CN(C)C=O.O>[CH:30]([O:33][C:34]1[CH:35]=[CH:36][C:37]([CH2:38][CH2:10][CH2:9][CH:5]2[O:4][CH2:8][CH2:7][O:6]2)=[CH:40][CH:41]=1)([CH3:32])[CH3:31]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 2500774-IsopropoxybenzaldehydeHCID 2733834Phosphonium, [2-(1,3-dioxolan-2-yl)ethyl]triphenyl-, bromide (1:1)

Product 1

HCID 108687092-[3-(4-Isopropoxyphenyl)propyl]-1,3-dioxolaneYield 24.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (oily, 60%, 4.60 g) was added little by little to a solution of 2-(1,3-dioxolan-2-yl)ethyltriphenylphosphonium bromide (51.0 g) in N,N-dimethylformamide (200 ml) at 0° C. After stirring for 15 minutes, 4-isopropoxybenzaldehyde (18.0 g) was added, and the mixture was stirred at 80 to 85° C. for 5 hours. Water was added to the reaction mixture, acidified with 2N hydrochloric acid, and extracted with ether. The ether layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel. An oil of the intermediate which was obtained from the fractions eluted with ethyl acetate-hexane (1:4, v/v) was dissolved in ethanol (250 ml), and 5% palladium-carbon (5.00 g) was added. The mixture was subjected to catalytic hydrogenation at 1 atm and room temperature. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions eluted with ethyl acetate-hexane (1:5, v/v) to give 2-[3-(4-isopropoxyphenyl)propyl]-1,3-dioxolane (6.70 g, 24%) as an oil.

Workup

  1. stirringthe mixture was stirred at 80 to 85° C. for 5 hours
  2. extractionextracted with ether
  3. washThe ether layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customAn oil of the intermediate which was obtained from the fractions
  7. washeluted with ethyl acetate-hexane (1:4, v/v)
  8. dissolutionwas dissolved in ethanol (250 ml)
  9. addition5% palladium-carbon (5.00 g) was added
  10. customwas subjected to catalytic hydrogenation at 1 atm and room temperature
  11. filtrationThe catalyst was filtered off
  12. concentrationthe filtrate was concentrated under reduced pressure
  13. washThe fractions eluted with ethyl acetate-hexane (1:5

Sources & evidence

ORD record
ord-204502b42a564d40a8748a368c12ba21
Source dataset
uspto-grants-1999_10
Patent number
US05965589

Reaction notes

Loading…