2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 54519904, compound

HRID 978316Notes

Reaction equation

HRID 978316 reaction equation
ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[CH3:15][C:16]1[C:24]2[CH2:23][CH2:22][O:21][C:20]=2[C:19]([CH:25]=[CH:26][C:27](=[O:29])[CH3:28])=[C:18]([CH3:30])[C:17]=1[CH3:31]>C1(C)C=CC=CC=1>[CH3:15][C:16]1[C:24]2[CH:23]=[CH:22][O:21][C:20]=2[C:19]([CH:25]=[CH:26][C:27](=[O:29])[CH3:28])=[C:18]([CH3:30])[C:17]=1[CH3:31]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 544769994-(4,5,6-Trimethyl-2,3-dihydro-1-benzofuran-7-yl)but-3-en-2-one

Product 1

HCID 54519904HCID 54519904, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (5.0 g) was added to a solution of 1-(4,5,6-trimethyl-2,3-dihydrobenzo[b]furan-7-yl)-but-1-en-3-one (5.0 g) in toluene (100 ml) and the mixture was stirred at room temperature for a period of 24 hours. The solvent was evaporated by distillation under reduced pressure and the residue was purified by column chromatography over silica gel with dichloromethane elution to give 1-(4,5,6-trimethylbenzo[b]furan-7-yl)but-1-en-3-one (4.2 g; 85%) as a pale yellow solid, mp 99° C.

Workup

  1. customThe solvent was evaporated by distillation under reduced pressure
  2. customthe residue was purified by column chromatography over silica gel with dichloromethane elution

Sources & evidence

ORD record
ord-9b3777badfb74613801d4d837f9cf21a
Source dataset
uspto-grants-1987_05
Patent number
US04664693

Reaction notes

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