3-Hydroxybenzaldehyde → 3-Methoxybenzaldehyde

HRID 1453072Notes

Reaction equation

HRID 1453072 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[C:10]([O-])([O-])=O.[K+].[K+].CI.O>CC(C)=O>[CH3:10][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium Carbonate

Product 1

HCID 115693-MethoxybenzaldehydeYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 3-hydroxybenzaldehyde (1.22 g, 10 mmol) in anhydrous acetone (50 mL) was treated with K2CO3 (2.76 g, 20 mmol) and MeI (0.9 mL, 15 mmol) at room temperature for 12 hours. The mixture was poured into water and extracted with EtOAc (3×30 mL). The combined organic layers were washed with brine and dried over Na2SO4. The solvent was removed and the product was purified by flash column chromatography (0-15% EtOAc in hexanes, 1.2 g, 88% yield). 1H NMR (300 MHz, CDCl3) δ: 3.88 (s, 3H), 7.17-7.21 (m, 1H), 7.38-7.42 (m, 1H), 7.45-7.47 (m, 2H), 9.99 (s, 1H).

Workup

  1. extractionextracted with EtOAc (3×30 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed
  5. customthe product was purified by flash column chromatography (0-15% EtOAc in hexanes, 1.2 g, 88% yield)

Sources & evidence

ORD record
ord-6733459e957247e2aa60304143cbfacd
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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