Methyl iodide → Methyl 3-hydroxy-5-methoxybenzoate

HRID 1177073Notes

Reaction equation

HRID 1177073 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([O:11][CH2:12]C=C)[CH:5]=1.CI.C([O-])([O-])=O.[K+].[K+].OC1C=C(C=C(O)C=1)C(OC)=O>>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:5]=[C:6]([O:11][CH3:12])[CH:7]=[C:8]([OH:10])[CH:9]=1

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 75076Methyl 3,5-DihydroxybenzoateHCID 595599953-Allyloxy-5-hydroxybenzoic acid methyl ester

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

  1. customPurification by column chromatography
  2. washeluting with 15% EtOAc in hexanes

Sources & evidence

ORD record
ord-31b55bcb6c8a46f894e53d2009bd214f
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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