3-Hydroxybenzaldehyde → 3-(4-Methylphenoxy)benzaldehyde

HRID 1678581Notes

Reaction equation

HRID 1678581 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH3:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl>[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[CH:5]=[O:6])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 8471TriethylamineHCID 79799Tolylboronic acid

Product 1

HCID 6113073-(4-Methylphenoxy)benzaldehydeYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Hydroxybenzaldehyde (1.0 g, 8.2 mmol) was dissolved in dichloromethane (50 mL). (4-Methylphenyl)boronic acid (2.2 g, 16.4 mmol), triethylamine (5.7 mL, 41.0 mmol) and copper acetate(II) (1.5 g, 8.2 mmol) were added thereto, and then the mixture was stirred at room temperature for 2 days. The reaction solution was filtered, and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=100:0 to 70:30) to give the title compound (324 mg, yield 19%).

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=100:0 to 70:30)

Sources & evidence

ORD record
ord-435bf42d60454fdf8ca49b3d94b55299
Source dataset
uspto-grants-2011_08
Patent number
US08008525B2

Reaction notes

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