Ethylene Glycol → HCID 13498876, compound

HRID 1196131Notes

Reaction equation

HRID 1196131 reaction equation
F[C:2]1[CH:19]=[CH:18][C:17]2[C:16](=[O:20])[C:15]3[C:6](=[CH:7][C:8]4[C:13]([CH:14]=3)=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:5](=[O:21])[C:4]=2[CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:28]([OH:31])[CH2:29][OH:30].Cl>O>[OH:30][CH2:29][CH2:28][O:31][C:2]1[CH:19]=[CH:18][C:17]2[C:16](=[O:20])[C:15]3[C:6](=[CH:7][C:8]4[C:13]([CH:14]=3)=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:5](=[O:21])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 200898282-Fluorotetracene-5,12-dione

Product 1

HCID 13498876HCID 13498876, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

27.6 g (0.1 mol) of 2-fluoro-5,12-naphthacenequinone, 32.5 g (0.1 mol) of Cs2CO3 and 300 ml of ethylene glycol are introduced into a sulfonating flask under nitrogen. After heating to 125° C., the mixture is stirred for 3 h. The reaction mixture is then poured into 3000 ml of water containing hydrochloric acid and the product which has precipitated is filtered off and washed several times with water. After drying in vacuo at 80° C., 30.3 g (97.1%) of pure product are obtained, melting point 208.8° C. The procedure is analogous in Examples 19-23 (see Table 2).

Workup

  1. customthe product which has precipitated
  2. filtrationis filtered off
  3. washwashed several times with water
  4. customAfter drying in vacuo at 80° C.

Sources & evidence

ORD record
ord-a7cba04c718343c09ef1c056401f8b86
Source dataset
uspto-grants-1992_05
Patent number
US05112977

Reaction notes

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