Formaldehyde → 8H-5,9,11-trioxabenzo[de]anthracene-4,6-dione

HRID 566990Notes

Reaction equation

HRID 566990 reaction equation
[CH:1]1[CH:10]=[C:9]2[C:11]([O:13][C:14](=[O:15])[C:7]3=[C:8]2[C:3](=[C:4]([OH:16])[CH:5]=[CH:6]3)[CH:2]=1)=[O:12].C=O.S(=O)(=O)(O)O.[O:24]1[CH2:29]COC[CH2:25]1>>[CH:2]1[C:3]2[C:8]3[C:9]([C:11](=[O:12])[O:13][C:14](=[O:15])[C:7]=3[CH:6]=[C:5]3[C:4]=2[O:16][CH2:29][O:24][CH2:25]3)=[CH:10][CH:1]=1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 312751,4-DioxaneHCID 59994974-Hydroxy-1,8-naphthalenedicarboxylic anhydride

Product 1

HCID 226239078H-5,9,11-trioxabenzo[de]anthracene-4,6-dione

Procedure

To a suspension of 620 mg (2.9 mmol) of 4-hydroxy-1,8-naphthalic anhydride (from Example S3) and 1.60 g (53.0 mmol) of paraformaldehyde in 20 mL dioxane was added 5.2 mL of concentrated sulfuric acid. The reaction mixture was refluxed for 1 hour and quenched with 100 mL water. The precipitate was isolated, dried, recrystallized from DMSO, washed with acetone, and dried again to yield 0.50 g of the title compound.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. customquenched with 100 mL water
  3. customThe precipitate was isolated
  4. customdried
  5. customrecrystallized from DMSO
  6. washwashed with acetone
  7. customdried again

Sources & evidence

ORD record
ord-608afc1d2b854351b5a0e93f18c0c67c
Source dataset
uspto-grants-2001_01
Patent number
US06177423B1

Reaction notes

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