Pyridine → 2-Methoxy-6-methyl-4-phenoxy-benzaldehyde

HRID 1798143Notes

Reaction equation

HRID 1798143 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([CH:6]=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1.C(Cl)Cl.[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.N1C=CC=CC=1>CC#N.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([O:1][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]=[C:8]([CH3:10])[C:5]=1[CH:6]=[O:7]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 66827Phenylboronic AcidHCID 143093964-Hydroxy-2-methoxy-6-methylbenzaldehyde

Product 1

HCID 582925842-Methoxy-6-methyl-4-phenoxy-benzaldehydeYield 63.1%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A suspension of 4-hydroxy-2-methoxy-6-methyl-benzaldehyde (1.00 g, 6.02 mmol), powdered 4A molecular sieves (4 g) in CH3CN (40 mL) and DCM (40 mL) was treated with phenylboronic acid (1.47 g, 12.06 mmol), followed by copper (II) acetate (1.09 g, 6.00 mmol). Pyridine (2.40 mL, 29.70 mmol) was added to the green suspension and the resulting mixture was stirred at rt overnight in an open flask. The mixture was filtered through a pad of Celite and the filtrate was concentrated to a green oil. The residue was purified by column chromatography (SiO2, EtOAc/hexanes; 1:9) to afford 2-methoxy-6-methyl-4-phenoxy-benzaldehyde (0.92 g, 63%), as a white solid. 1H NMR (400 MHz, CDCl3) δ 10.52 (s, 1H), 7.41 (t, J=7.42 Hz, 2H), 7.22 (t, J=7.42 Hz, 1H), 7.08 (d, J=7.42 Hz, 2H), 6.43 (d, J=2.34 Hz, 1H), 6.31 (d, J=2.34 Hz, 1H), 3.83 (s, 3H), 2.53 (s, 3H).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated to a green oil
  3. customThe residue was purified by column chromatography (SiO2, EtOAc/hexanes; 1:9)

Sources & evidence

ORD record
ord-285a7bb913c4431ba96ea82558a4629d
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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