2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Benzo[b]naphtho[2,1-d]furan

HRID 470728Notes

Reaction equation

HRID 470728 reaction equation
[CH:1]1[C:13]2[C:12]3[O:11][C:10]4[CH2:14][CH2:15][CH2:16][CH2:17][C:9]=4[C:8]=3[CH:7]=[CH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[CH:1]1[C:13]2[C:12]3[O:11][C:10]4[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=4[C:8]=3[CH:7]=[CH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 2685557,8,9,10-Tetrahydrobenzo[b]naphtho[2,1-d]furan

Product 1

HCID 67460Benzo[b]naphtho[2,1-d]furanYield 60%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In the atmosphere of argon, 55.5 g of 7,8,9,10-tetrahydrobenzo[b]naphtho[2,1-d]furan, 119 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and 1 L of anhydrous 1,4-dioxane were placed in a flask. The resulting mixture was stirred under reflux for 12 hours. After cooling to room temperature, the reaction solution was extracted with toluene, and deposited solids were filtered out. The filtrate was concentrated by means of a rotary evaporator, and residues were purified by silica gel column chromatography, whereby 32.7 g of (yield: 60%) of benzo[b]naphtho[2,1-d]furan was obtained.

Workup

  1. temperatureunder reflux for 12 hours
  2. extractionthe reaction solution was extracted with toluene
  3. filtrationwere filtered out
  4. concentrationThe filtrate was concentrated by means of a rotary evaporator, and residues
  5. customwere purified by silica gel column chromatography

Sources & evidence

ORD record
ord-873392e5700d4982a706ecc7d3047eff
Source dataset
uspto-grants-2014_01
Patent number
US08629430B2

Reaction notes

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