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

HRID 508806Notes

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

Reactant 4

HCID 57882-Hydroxy-p-toluic acid

HCID 6228Dimethylformamide

HCID 6328Methyl iodide

HCID 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

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

Sources & evidence

ORD record: ord-0f1f8584674f4c6fa7d748239e70c606
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096545B2

Reaction notes

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