2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 20267188, compound

HRID 1719564Notes

Reaction equation

HRID 1719564 reaction equation
[CH3:1][C:2]1([C:12]([O:14][CH3:15])=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[CH3:1][C:2]1([C:12]([O:14][CH3:15])=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH2:3]1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 13863238HCID 13863238, compound

Product 1

HCID 20267188HCID 20267188, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 24 g of methyl 3,4-dihydro-1-methylnaphthalenecarboxylate, 30 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and 400 ml of toluene was heated at reflux for 18 hours. The reaction mixture was then filtered and concentrated in vacuo. Sodium bisulfite solution (150 ml, 25%) was added to the residue, followed by 150 ml of toluene and 50 ml of ether. The latter mixture was washed twice with each of the following: 25% sodium bisulfite solution, concentrated sodium chloride solution, sodium bicarbonate solution and water. The organic solution was dried over anhydrous sodium sulfate and concentrated in vacuo to give 17.5 g of methyl 1-methylnaphthalenecarboxylate as an oil, which upon further purification gave the product in crystalline form, m.p. 48°-49° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. filtrationThe reaction mixture was then filtered
  4. concentrationconcentrated in vacuo
  5. additionSodium bisulfite solution (150 ml, 25%) was added to the residue
  6. washThe latter mixture was washed twice with each of the following: 25% sodium bisulfite solution, concentrated sodium chloride solution, sodium bicarbonate solution and water
  7. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5020308f38324894b4f19fc61aacfe03
Source dataset
uspto-grants-1985_09
Patent number
US04540705

Reaction notes

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