Methanol → HCID 10632802, compound

HRID 1019364Notes

Reaction equation

HRID 1019364 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[CH2:12][C:13]([OH:15])=[O:14])(=[O:3])[CH3:2].S(=O)(=O)(O)O.[CH3:21]O>>[CH3:21][O:14][C:13](=[O:15])[CH2:12][C:5]1[CH:6]=[C:7]([O:10][CH3:11])[CH:8]=[CH:9][C:4]=1[C:1](=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 18401031HCID 18401031, compound

Product 1

HCID 10632802HCID 10632802, compoundYield 88%

Procedure

To a solution of (2-acetyl-5-methoxy-phenyl)-acetic acid (5.00 g, 24.0 mmol) in methanol (50 mL) was added concentrated sulfuric acid (1.0 mL). The reaction mixture was stirred at room temperature for 16 hours after which it was concentrated to a low volume. Dichloromethane (50 mL) was added and the solution was washed with 1N sodium hydroxide (50 mL). The layers were separated and the organic layer was dried over magnesium sulfate, filtered, and concentrated to an oil which solidified on standing to afford (2-acetyl-5-methoxy-phenyl)-acetic acid methyl ester (4.70 g, 88%). M.p. 74-76° C. 1H NMR (300 MHz, CDCl3) δ2.58 (s, 3), 3.74 (s, 3), 3.89 (s, 3), 3.95 (s, 2), 6.78 (d, 1, J=2.6), 6.89 (dd, 1, J=8.7, 2.6), 7.89 (d, 1, J=8.6). 13C NMR (75 MHz, CDCl3) δ29.65, 42.35, 53.11, 56.69, 113.17, 120.00, 130.52, 134.39, 138.90, 163.54, 173.23, 200.35. IR 1739, 1665, 1605, 1568, 1321, 1247, 1165 cm−1. Analysis calculated for C12H14O4: C, 65.85; H, 6.35. Found: C, 64.87; H, 6.44.

Workup

  1. concentrationwas concentrated to a low volume
  2. additionDichloromethane (50 mL) was added
  3. washthe solution was washed with 1N sodium hydroxide (50 mL)
  4. customThe layers were separated
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to an oil which

Sources & evidence

ORD record
ord-c4ec8ebb54d34c5c8f6d15e2dde9778c
Source dataset
uspto-grants-2002_11
Patent number
US06486325B1

Reaction notes

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