Sulfuric Acid → Npc191948

HRID 1386403Notes

Reaction equation

HRID 1386403 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH2:16][CH2:17][C:18](O)=[O:19])[CH:12]=[CH:13][C:14]=1[CH3:15].OS(O)(=O)=O>C1COCC1>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH2:16][CH2:17][CH2:18][OH:19])[CH:12]=[CH:13][C:14]=1[CH3:15]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 31636013-(3-methoxy-4-methylphenyl)propanoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 10997638Npc191948Yield 91.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 3.3 g (98.1 mmol) of lithium aluminum hydride in 40 mL THF was treated dropwise with a solution of 8.65 g (44.5 mmol) of 3-(3-methoxy-4-methylphenyl)propanoic acid in 125 mL of THF. After stirring at room temperature for 0.5 hour, the mixture was heated at reflux for 2 hours. The mixture was cautiously acidified with 1N H2SO4, then extracted with EtOAc. The EtOAc was washed with 1N H2SO4, H2O, saturated NaHCO3, and saturated NaCl. Drying over MgSO4 and removal of the solvent under reduced pressure left 7.33 g (91.6% yield) of the product as a clear oil. The structure was confirmed by NMR and mass spectroscopy. MS m/z 181 (M+H+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 hours
  3. extractionextracted with EtOAc
  4. washThe EtOAc was washed with 1N H2SO4, H2O, saturated NaHCO3, and saturated NaCl
  5. dry with materialDrying over MgSO4 and removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-3973b1787d61488ba2a1eaa266436e3e
Source dataset
uspto-grants-2001_07
Patent number
US06265422B1

Reaction notes

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