3-Hydroxybenzaldehyde → 3-Methoxybenzaldehyde

HRID 858622Notes

Reaction equation

HRID 858622 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+].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

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 962WaterHCID 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 Mel (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, 3 H), 7.17–7.21 (m, 1 H), 7.38–7.42 (m, 1 H), 7.45–7.47 (m, 2 H), 9.99 (s, 1 H).

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-e0ab6fbd5c7d4c729d84a67255adb42c
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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