Acetic Acid → HCID 21516800, compound

HRID 1283877Notes

Reaction equation

HRID 1283877 reaction equation
[Cl:1][C:2]1[C:3](=[O:14])[C:4](C#N)=[C:5]([C:10]#N)[C:6](=O)[C:7]=1[Cl:8].[CH:15]1[CH:20]=CC=[CH:17][CH:16]=1.[C:21]([OH:24])(=O)[CH3:22].S(=O)(O)[O-].[Na+].[C:30](OCC)(=O)C>>[Cl:8][C:7]1[C:6]2[C:21](=[O:24])[C:22]3[C:10](=[CH:20][CH:15]=[CH:16][CH:17]=3)[C:5]=2[CH:4]=[C:3]([O:14][CH3:30])[C:2]=1[Cl:1]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 241BenzeneHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 8857Ethyl AcetateHCID 23665763Sodium Bisulfite

Product 1

HCID 21516800HCID 21516800, compound

Procedure

A stirred mixture of 1α,1,2,3,4,4α-hexahydro- 6-methoxy-7,8-dichlorofluoren-9-one (8.3 g., 0.029 mole), 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (20.5 g., 0.091 mole), benzene (300 ml.) and acetic acid (10 ml.) is heated at reflux under nitrogen for 64 hours. The reaction mixture is dissolved in a large volume of ethyl acetate (3 l.), the organic solution treated with sodium bisulfite solution, washed with water, 5% sodium hydroxide solution and water, separated, dried over magnesium sulfate and concentrated to give 1,2-dichloro-3-methoxyfluoren-9-one which after sublimation and trituration with acetonitrile give 3.9 g. melting at 268°-270°C.

Workup

  1. temperatureis heated
  2. temperatureat reflux under nitrogen for 64 hours
  3. washwashed with water, 5% sodium hydroxide solution and water
  4. customseparated
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-95e9e2592bac45d0872cdadfbc9518e4
Source dataset
uspto-grants-1976_08
Patent number
US03976686

Reaction notes

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