Sulfuric Acid → 4-(2-Methoxy-5-methylphenyl)butanoic acid

HRID 2290928Notes

Reaction equation

HRID 2290928 reaction equation
O=[C:2]([C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=1[O:15][CH3:16])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].OS(O)(=O)=O>[Pd].CC(O)=O>[CH3:16][O:15][C:9]1[CH:10]=[CH:11][C:12]([CH3:14])=[CH:13][C:8]=1[CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 2989124-(2-Methoxy-5-methylphenyl)-4-oxobutanoic acid

Product 1

HCID 2824524-(2-Methoxy-5-methylphenyl)butanoic acidYield 64.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 4-Keto-γ-(2-methoxy-5-methylphenyl)butyric acid (123 g, 0.55 mole), HOAc (1.5 L), and H2SO4 (3.2 mL) in the presence of Pd/C catalyst (12.2 g, dry) was hydrogenated under 3 atmospheres H2 pressure for 3 hours at room temperature. The resulting solution was filtered and was evaporated to the volume of 100 mL. Water (1000 mL) was added with stirring. The solid was filtered, dried (in-vacuo), and was recrystallized from ether/hexane to yield 74 g white solid,, (64%); m+ 208.

Workup

  1. filtrationThe resulting solution was filtered
  2. customwas evaporated to the volume of 100 mL
  3. additionWater (1000 mL) was added
  4. filtrationThe solid was filtered
  5. customdried (in-vacuo)
  6. customwas recrystallized from ether/hexane

Sources & evidence

ORD record
ord-2f2351268aa94862838e9dc1274c082c
Source dataset
uspto-grants-1986_10
Patent number
US04618683

Reaction notes

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