3-(3-Methoxyphenyl)-3-methylbutanoic acid → Methyl 3-(3-methoxyphenyl)-3-methylbutanoate

HRID 1662558Notes

Reaction equation

HRID 1662558 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([CH3:15])([CH3:14])[CH2:10][C:11]([OH:13])=[O:12])[CH:6]=[CH:7][CH:8]=1.[C:16](=O)(O)[O-].[Na+]>CO.S(=O)(=O)(O)O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([CH3:15])([CH3:14])[CH2:10][C:11]([O:13][CH3:16])=[O:12])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 3167483-(3-Methoxyphenyl)-3-methylbutanoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 57705813Methyl 3-(3-methoxyphenyl)-3-methylbutanoateYield 97%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Procedure

3-(3-Methoxyphenyl)-3-methylbutanoic acid 85.D (0.22 g, 1.1 mmol) was dissolved in MeOH (11 mL) and a catalytic amount (˜5 drops) of sulfuric acid was added. The solution was heated to reflux and stirred overnight. The reaction was cooled to room temperature and saturated sodium bicarbonate was added to neutralize the reaction. The mixture was then concentrated and the residue taken up in EtOAc and washed with water (2×30 mL), 1M lithium chloride solution (1×30 mL) and brine (1×30 mL) and dried over magnesium sulfate to give the desired product methyl 3-(3-methoxyphenyl)-3-methylbutanoate 85.E (0.227 g, 97% yield). MS ESI (pos.) m/e: 240.1 (M+H2O)+.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. customthe reaction
  4. concentrationThe mixture was then concentrated
  5. washwashed with water (2×30 mL), 1M lithium chloride solution (1×30 mL) and brine (1×30 mL)
  6. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-0345b17e9a2c492aa8037e86ff7ecc38
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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