Thionyl Chloride → 4,9-Bis(ethyloxy)naphtho[2,3-c]furan-1,3-dione

HRID 889482Notes

Reaction equation

HRID 889482 reaction equation
[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][CH2:15][CH3:16])=[C:6]([C:17]([OH:19])=O)[C:5]=1[C:20]([OH:22])=[O:21])[CH3:2].S(Cl)(Cl)=O>C(Cl)(Cl)Cl>[CH2:15]([O:14][C:7]1[C:6]2[C:17](=[O:19])[O:21][C:20](=[O:22])[C:5]=2[C:4]([O:3][CH2:1][CH3:2])=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[CH:12]2)[CH3:16]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 223445251,4-Diethoxynaphthalene-2,3-dicarboxylic acid

Product 1

HCID 207619774,9-Bis(ethyloxy)naphtho[2,3-c]furan-1,3-dione

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
65 °C

Procedure

1,4-Bis(ethyloxy)-2,3-naphthalenedicarboxylic acid (10.3 g, 33.8 mmol) was added to a three neck flask and chloroform (80 ml) added and stirred. Thionyl chloride (49.2 ml, 355.4 mmol) in a dropping funnel was added dropwise over 25 minutes whilst monitoring temperature (no change). The reaction was heated at relfux (65° C.) overnight. LC/MS indicated no starting material remained. Reaction mixture was cooled to room temperature and solvent evaporated. The product was azeotroped with chloroform (×2) to remove the remaining traces of thionyl chloride to give the title compound as*a pale yellow solid (9.86 g).

Workup

  1. additionadded
  2. customReaction mixture
  3. temperaturewas cooled to room temperature
  4. customsolvent evaporated
  5. customThe product was azeotroped with chloroform (×2)
  6. customto remove the remaining traces of thionyl chloride

Sources & evidence

ORD record
ord-85e043741f284032a2a7e2f56f77f5b0
Source dataset
uspto-grants-2012_08
Patent number
US08252833B2

Reaction notes

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