Ethyl Acetate → HCID 17861380, compound

HRID 1294098Notes

Reaction equation

HRID 1294098 reaction equation
CSCS(C)=O.[OH-].[Na+].C([O:16][C:17]1[CH:18]=[CH:19][C:20]([O:25][CH2:26][CH3:27])=[C:21]([CH:24]=1)[CH:22]=O)C1C=CC=CC=1.[C:28]([O:31][CH2:32]C)(=[O:30])C>>[CH2:26]([O:25][C:20]1[CH:19]=[CH:18][C:17]([OH:16])=[CH:24][C:21]=1[CH2:22][C:28]([O:31][CH3:32])=[O:30])[CH3:27]

Participants

5

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 99129Methyl (methylsulfinyl)methyl sulfideHCID 3839920HCID 3839920, compound

Product 1

HCID 17861380HCID 17861380, compoundYield 44%

Conditions

Temperature
70 °C

Procedure

A mixture of methyl methylthiomethyl sulfoxide. (0.30 g) and finely triturated sodium hydroxide (0.015 g) was stirred at 70° C. for 30 min. To the reaction mixture was added 5-benzyloxy-2-ethoxybenzaldehyde (0.30 g), and the mixture was further stirred at 70° C. for 1.5 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 (15 mL) was heated under reflux for 15 hrs. To the reaction mixture was added ethyl acetate. 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-ethoxy-5-hydroxyphenyl)acetate as a colorless oil (0.11 g, 44%) from a fraction eluted with ethyl acetate-hexane (1:4, v/v).

Workup

  1. washthe organic layer was washed successively with 1N hydrochloric acid and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. additionA mixture of the obtained residue and 10% hydrogen chloride-methanol (15 mL)
  5. temperaturewas heated
  6. temperatureunder reflux for 15 hrs
  7. additionTo the reaction mixture was added ethyl acetate
  8. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-349d809b067b48588767e17048692769
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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