Hydrochloric Acid → Methyl 2-methyl-2-phenylpropanoate

HRID 502395Notes

Reaction equation

HRID 502395 reaction equation
[CH3:1][C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:6])[C:3]([OH:5])=[O:4].[C:13](=O)([O-])O.[Na+].CI.Cl>CN(C)C=O>[CH3:13][O:4][C:3](=[O:5])[C:2]([CH3:1])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 132222-Phenylisobutyric acidHCID 516892Sodium Bicarbonate

Product 1

HCID 143498Methyl 2-methyl-2-phenylpropanoateYield 74.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9.00 g (55 mmol) 2-methyl-2-phenyl-propionic acid was dissolved in 90 ml N,N-dimethylformamide, 11.51 g (2.5 eq.) of sodium hydrogencarbonate was added followed by 6.89 mL (15.72 g 2 eq.) of methyl iodide. The mixture was stirred at rt for 40 hours, then poured into ice water, the pH was adjusted to ˜3.0 with aq. HCl (1N) and the mixture extracted 3 times with ether; the organic phases were washed with water, dried over MgSO4, filtered and evaporated to give 7.34 g of the crude title compound as yellow oil. MS: 178.1 (M+).

Workup

  1. extractionthe mixture extracted 3 times with ether
  2. washthe organic phases were washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-790ae699c2ab45e6b3c8bf0d08eff6d7
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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