Sulfuric Acid → 4-(4-Tolyl)butanoic acid methyl ester

HRID 51159Notes

Reaction equation

HRID 51159 reaction equation
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[C:19](=O)(O)[O-].[Na+]>CO>[C:1]1([CH3:13])[CH:2]=[CH:3][C:4]([CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:19])=[O:11])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 782794-p-Tolylbutyric acidHCID 516892Sodium Bicarbonate

Product 1

HCID 322824-(4-Tolyl)butanoic acid methyl esterYield 100.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(p-tolyl)-butyric acid (10.0 g, 56.11 mmol) in methanol (680 mL) was treated with concentrated sulfuric acid (5.4 mL). The reaction was stirred at room temperature for 18 hour. Sodium bicarbonate (˜15 g) was added and the mixture was stirred for 15 minutes, then concentrated. The residue was dissolved in ethyl acetate/water. The organic phase was separated and washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated to give the title material (10.8 g, 100% crude) as an oil which was used for the next reaction.

Workup

  1. stirringthe mixture was stirred for 15 minutes
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in ethyl acetate/water
  4. customThe organic phase was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1399f1dff8ea4ddc9db22ad28fee824c
Source dataset
uspto-grants-2004_03
Patent number
US06713515B2

Reaction notes

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