Methanol → Methyl 2-(2-benzyloxy-5-ethoxyphenyl)acetate

HRID 1294129Notes

Reaction equation

HRID 1294129 reaction equation
CSCS(C)=O.[CH2:7]([O:14][C:15]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH3:25])=[CH:19][C:16]=1[CH:17]=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CO.[C:28]([O:31][CH2:32]C)(=[O:30])C>[OH-].[Na+]>[CH2:7]([O:14][C:15]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH3:25])=[CH:19][C:16]=1[CH2:17][C:28]([O:31][CH3:32])=[O:30])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 99129Methyl (methylsulfinyl)methyl sulfideHCID 178612542-Benzyloxy-5-ethoxybenzaldehyde

Product 1

HCID 17861303Methyl 2-(2-benzyloxy-5-ethoxyphenyl)acetateYield 69%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideCatalyst

Conditions

Temperature
70 °C

Procedure

A mixture of methyl methylthiomethyl sulfoxide (1.94 g) and finely triturated sodium hydroxide (0.01 g) was stirred at 70° C. for 30 min. 2-Benzyloxy-5-ethoxybenzaldehyde (2.0 g) and methanol (10 mL) were added to the reaction mixture, and the mixture was further heated under reflux for 24 hrs. To the reaction mixture was added ethyl acetate, and the organic layer was washed successively with 1N hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. A mixture of the obtained residue and 10% hydrogen chloride-methanol (100 mL) was heated under reflux for 24 hrs. The reaction mixture was concentrated, and then ethyl acetate was added to the residue. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to give methyl 2-(2-benzyloxy-5-ethoxyphenyl)acetate as a yellow oil (1.60 g, 69%) from a fraction eluted with ethyl acetate-hexane (1:3, v/v).

Workup

  1. temperaturethe mixture was further heated
  2. temperatureunder reflux for 24 hrs
  3. washthe organic layer was washed successively with 1N hydrochloric acid and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. additionA mixture of the obtained residue and 10% hydrogen chloride-methanol (100 mL)
  7. temperaturewas heated
  8. temperatureunder reflux for 24 hrs
  9. concentrationThe reaction mixture was concentrated
  10. additionethyl acetate was added to the residue
  11. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-f908bf50a2bf4c4486d07e983290d035
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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