Methanol → Methyl Syringate

HRID 1830970Notes

Reaction equation

HRID 1830970 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) δ3.9 (s, 3H), 3.95 (s, 3H), 3.975 (s, 3H), 6.1 (s, 1H), 7.3 (s, 2H); 13C NMR (67.8 MHz, CDCl3) 3 166.9, 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-c65623f98d7f44edb656ab88d58e5d61
Source dataset
uspto-grants-2006_06
Patent number
US07067511B2

Reaction notes

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