Methanol → Methyl 3-acetylbenzoate

HRID 912036Notes

Reaction equation

HRID 912036 reaction equation
S(=O)(=O)(O)O.CO.[C:8]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14]([OH:16])=[O:15])(=[O:10])[CH3:9].[C:20]([O-])(O)=O.[Na+]>O>[CH3:20][O:15][C:14](=[O:16])[C:13]1[CH:17]=[CH:18][CH:19]=[C:11]([C:8](=[O:10])[CH3:9])[CH:12]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2203243-Acetylbenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 15094405Methyl 3-acetylbenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Sulfuric acid (23.4 μl, 0.430 mmol) was added into the MeOH (15 ml) solution of 3-acetylbenzoic acid (720 mg, 4.30 mmol). The mixture was stirred at 70° C. for 20 h. After that time, the mixture was cooled and was treated with saturated NaHCO3 till pH>9, followed by adding water to dissolve the solid which was formed, extracted with EtOAc (2×50 ml). The extracts were washed with water (50 ml), brine (50 ml), dried over MgSO4, filtered and concentrated in vacuo, giving the title compound as brown oil. 1H NMR (400 MHz, CDCl3): δ=2.66 (s, 3H), 3.96 (s, 3H), 7.54-7.59 (m, 1H), 8.14-8.19 (m, 1H), 8.22-8.26 (m, 1H), 8.59-8.61 (m, 1H). MS (ES+): m/z 179.17 [MH+]. HPLC: tR=2.82 min (polar—5 min, ZQ3).

Workup

  1. temperatureAfter that time, the mixture was cooled
  2. dissolutionto dissolve the solid which
  3. customwas formed
  4. extractionextracted with EtOAc (2×50 ml)
  5. washThe extracts were washed with water (50 ml), brine (50 ml)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-544aef6706cf4f8bb2241eae6dbba859
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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