Methanol → Methyl Syringate

HRID 1826137Notes

Reaction equation

HRID 1826137 reaction equation
S(=O)(=O)(O)O.[C:6]([OH:19])(=[O:18])[C:7]1[CH:17]=[C:14]([O:15][CH3:16])[C:12]([OH:13])=[C:9]([O:10][CH3:11])[CH:8]=1.[CH3:20]O>>[OH:13][C:12]1[C:14]([O:15][CH3:16])=[CH:17][C:7]([C:6]([O:19][CH3:20])=[O:18])=[CH:8][C:9]=1[O:10][CH3:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 10742Syringic Acid

Product 1

HCID 70164Methyl Syringate

Procedure

Concentrated sulphuric acid (3 mL), was added dropwise to a solution of 81 (20.24 g, 102.1 mmol) in refluxing methanol (70 mL). The reaction mixture was heated at reflux for a further 5 hours and then cooled to room temperature and concentrated to a third of its original volume. The concentrate was poured onto crushed ice (c. 150 mL) and allowed to stand for 30 minutes. The aqueous mixture was extracted with ethyl acetate (3×100 mL) and the combined organic phase washed with distilled water (3×100 mL), brine (3×100 mL) and dried over anhydrous MgSO4. Removal of ecxess solvent under reduced pressure afforded the product as a yellow solid, 121 (18.39 g, 86.7 mmol; 1H NMR (270 MHz, CDCl3) δ 3.9 (s, 3H), 3.95 (s, 3H), 3.975 (s, 3H), 6.1 (s, 1H), 7.3 (s, 2H); 13C NMR (67.8 MHz, CDCl3) δ 166.9, 146.6, 139.2, 121.0, 106.6, 56.4, 52.1.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for a further 5 hours
  3. concentrationconcentrated to a third of its original volume
  4. additionThe concentrate was poured
  5. customonto crushed ice (c. 150 mL)
  6. extractionThe aqueous mixture was extracted with ethyl acetate (3×100 mL)
  7. washthe combined organic phase washed with distilled water (3×100 mL), brine (3×100 mL)
  8. dry with materialdried over anhydrous MgSO4
  9. customRemoval of ecxess solvent under reduced pressure

Sources & evidence

ORD record
ord-d43c5f503f4f4818b75e78ad358da63f
Source dataset
uspto-grants-2006_05
Patent number
US07049311B1

Reaction notes

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