Ethanol → Ethyl 2-(3,4-dimethoxyphenyl)-2-methylpropanoate

HRID 1627395Notes

Reaction equation

HRID 1627395 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH3:16])([CH3:15])[C:12]([OH:14])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].OS(O)(=O)=O.[CH3:22][CH2:23]O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH3:16])([CH3:15])[C:12]([O:14][CH2:22][CH3:23])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 122597132-(3,4-DIMETHOXYPHENYL)-2-METHYLPROPANOIC ACID

Product 1

HCID 20523075Ethyl 2-(3,4-dimethoxyphenyl)-2-methylpropanoate

Procedure

A solution of 2-(3,4-dimethoxyphenyl)-2-methylpropanoic acid (2.5 g, 11.15 mmol) in EtOH (50 mL) with H2SO4 (cat.) was heated at reflux 12 h. The mixture was cooled to room temperature and the solvent was evaporated under reduced pressure. The residue was dissolved in EtOAc and washed with satd NaHCO3 and brine. The organic layer was dried over MgSO4, filtered and concentrated to give ethyl 2-(3,4-dimethoxyphenyl)-2-methylpropanoate (2.81 g, quant), which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 6.95-6.78 (m, 3H), 4.14 (q, 2H), 3.88 (s, 3H), 3.87 (s, 3H), 1.56 (s, 6H), 1.19 (t. 3H).

Workup

  1. temperatureat reflux 12 h
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with satd NaHCO3 and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-905bafa706184d05b3f63e0d7c5535ac
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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