Methyl iodide → Methyl 3-hydroxy-5-methoxybenzoate

HRID 1643546Notes

Reaction equation

CI.[C:3]([O-])([O-])=O.[K+].[K+].[OH:9][C:10]1[CH:11]=[C:12]([CH:17]=[C:18]([OH:20])[CH:19]=1)[C:13]([O:15][CH3:16])=[O:14]>>[CH3:16][O:15][C:13](=[O:14])[C:12]1[CH:11]=[C:10]([O:9][CH3:3])[CH:19]=[C:18]([OH:20])[CH:17]=1

Participants

Reactant 3

HCID 6328Methyl iodide

HCID 11430Potassium Carbonate

HCID 75076Methyl 3,5-Dihydroxybenzoate

Product 1

HCID 13941268Methyl 3-hydroxy-5-methoxybenzoate

Procedure

The title compound was prepared in a similar manner as described for Intermediate 1a, from methyl iodide (6.44 mL, 104 mmol), K2CO3 (28.8 g, 208.15 mmol), and methyl 3,5-dihydroxybenzoate (17.5 g, 64 mmol). Purification by column chromatography eluting with 15% EtOAc in hexanes gave a pale yellow solid (7.51 g, 40% yield). 1H NMR (400 MHz, CDCl3) δ 7.16 (dd, J=4.80, 2.27 Hz, 2 H) 6.63 (t, J=2.27 Hz, 1 H) 5.36 (s, 1H) 3.92 (s, 3 H) 3.83 (s, 3 H).

Workup

customPurification by column chromatography
washeluting with 15% EtOAc in hexanes

Sources & evidence

ORD record: ord-b0bc291c6e044113ac204ab29e65da75
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119624B2

Reaction notes

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