Diethyl Ether → 4-Methoxybenzofuran-3(2H)-one

HRID 381727Notes

Reaction equation

HRID 381727 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.ClCC#N.[CH3:14][CH2:15][O:16]CC>[Cl-].[Cl-].[Zn+2]>[CH3:1][O:2][C:3]1[C:4]2[C:15](=[O:16])[CH2:14][O:9][C:5]=2[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 7856ChloroacetonitrileHCID 90073-Methoxyphenol

Product 1

HCID 6391464-Methoxybenzofuran-3(2H)-oneYield 13%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

These compounds were prepared from 3-methoxyphenol (1) (6 ml, 55 mmol), ZnCl2 (8.2 g, 60 mmol), and chloroacetonitrile (4.2 g, 66 mmol) in dry ether (100 ml). Purification of the crude product by column chromatography (eluent: CH2Cl2/MeOH: 99/1) gave (2) (1.147 g, 13%), a single compound by HPLC (98% pure, recrystallized from EtOH). 1H-NMR (Acetone-d6, 400 MHz): (7.45 (1 H, d); 6.64 (2 H, m); 4.62 (s, 2 H); 3.95 (s, 3 H) and the more polar compound (3) (1.48 g, 17%). HPLC (84% purity). 1H-NMR (Acetone -d6): δ (400 MHz): values corresponded to previous synthesis of (3).

Workup

  1. customPurification of the crude product by column chromatography (eluent: CH2Cl2/MeOH: 99/1)

Sources & evidence

ORD record
ord-5a026d974146498da64fbe524ccdad28
Source dataset
uspto-grants-2001_10
Patent number
US06307070B1

Reaction notes

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