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

HRID 2285326Notes

Reaction equation

HRID 2285326 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-ad240d468fd54073b45cbae01eab3ddf
Source dataset
uspto-grants-2015_09
Patent number
US09147847B2

Reaction notes

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