2-Hydroxy-p-toluic acid → Methyl 2-methoxy-4-methylbenzoate

HRID 59313

Reaction equation

HRID 59313 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[C:12]([O-])([O-])=O.[K+].[K+].CI.CN([CH:23]=[O:24])C>>[CH3:12][O:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:24][CH3:23])=[O:5]

Participants

5

Reactant 4

HCID 57882-Hydroxy-p-toluic acidHCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium Carbonate

Product 1

HCID 7172021Methyl 2-methoxy-4-methylbenzoate

Conditions

Temperature
60 °C

Procedure

To a solution of 2-hydroxy-4-methylbenzoic acid (10.00 g, 65 mmol) in DMF (10 mL) was added K2CO3 (13.6 g, 98 mmol). The reaction mixture was stirred at 60° C. for 1 h. Methyl iodide (14.0 g, 98 mmol) was added to the reaction mixture and was stirred at 60° C. for 18 h. The reaction mass was quenched in water and concentrated. The reaction mass was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 10.00 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 2.34 (s, 3H), 3.74 (s, 3H), 3.79 (s, 3H), 6.81 (d, J=7.2 Hz, 1H), 6.97 (s, 1H), 7.56 (d, J=7.8 Hz, 1H); MS (m/z): 180.95 (M+H)+.

Workup

  1. stirringwas stirred at 60° C. for 18 h
  2. customThe reaction mass was quenched in water
  3. concentrationconcentrated
  4. extractionThe reaction mass was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a779c0a97d594d48bc1125917c241a90
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Linked notes

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