Sulfuric acid magnesium salt (1:1) → Methyl 4-butyrylbenzoate

HRID 2407014Notes

Reaction equation

HRID 2407014 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[OH:12][CH:13]([C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1)[CH2:14][CH2:15][CH3:16].[O-]S([O-])(=O)=O.[Mg+2]>ClCCl>[C:13]([C:17]1[CH:18]=[CH:19][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:25][CH:26]=1)(=[O:12])[CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 10443031HCID 10443031, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 23143286Methyl 4-butyrylbenzoateYield 82.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinium chlorochromate (1.25 g, 5.80 mmol) was added to a 0° C. solution of methyl 4-(1-hydroxybutyl)benzoate (602.5 mg, 2.89 mmol) in 9.6 mL dichloromethane. The reaction mixture was allowed to warm to room temperature and stirred for 3 h. MgSO4 was added, and the solids removed by filtration. The filtrate was concentrated to give a brown solid. Purification by silica gel chromatography provided methyl 4-butyrylbenzoate (491.2 mg) as a colorless solid. 1H NMR (400 MHz, CDCl3, δ): 8.08-8.13 (m, 2H), 7.97-8.01 (m, 2H), 3.94 (s, 3H), 2.96 (t, J=7.3 Hz, 2H), 1.77 (m, 2H), 1.00 (t, J=7.41 Hz, 3H).

Workup

  1. customthe solids removed by filtration
  2. concentrationThe filtrate was concentrated
  3. customto give a brown solid
  4. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-4ca948a90ac74238922d0939430b8314
Source dataset
uspto-grants-2014_08
Patent number
US08809342B2

Reaction notes

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