Methanol → Methyl 2,10-dimethyl-12H-dibenzo[d,g][1,3]dioxocin-6-carboxylate

HRID 1579220Notes

Reaction equation

HRID 1579220 reaction equation
[CH3:1][C:2]1[CH:21]=[CH:20][C:5]2[O:6][CH:7]([C:17]([OH:19])=[O:18])[O:8][C:9]3[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:10]=3[CH2:11][C:4]=2[CH:3]=1.S(=O)(=O)(O)O.[CH3:27]O>>[CH3:1][C:2]1[CH:21]=[CH:20][C:5]2[O:6][CH:7]([C:17]([O:19][CH3:27])=[O:18])[O:8][C:9]3[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:10]=3[CH2:11][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 21568148HCID 21568148, compound

Product 1

HCID 21568131Methyl 2,10-dimethyl-12H-dibenzo[d,g][1,3]dioxocin-6-carboxylate

Procedure

The carboxylic acid was dissolved in 300 ml of methanol and 2 ml of concentrated sulfuric acid was added. The mixture was refluxed for 1 hour, cooled, the resulting crystals collected and recrystallized from methanol-acetone to give methyl 2,10-dimethyl-12H-dibenzo[d,g][1,3]dioxocin-6-carboxylate, m.p. 158°-160°C. The methyl ester and excess diethylamine are refluxed for 16 hours. The remaining diethylamine is removed, and N,N-diethyl-2,10-dimethyl-12H-dibenzo[d,g][1,3]dioxocin-6-carboxamide is obtained.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. temperaturecooled
  3. customthe resulting crystals collected
  4. customrecrystallized from methanol-acetone

Sources & evidence

ORD record
ord-1bc58250c0f5470aa84133f5a19f3419
Source dataset
uspto-grants-1976_01
Patent number
US03931173

Reaction notes

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