Methanol → HCID 15679049, compound

HRID 1111274Notes

Reaction equation

HRID 1111274 reaction equation
[CH3:1][C:2]1[C:7]2[O:8][CH:9]([C:18]([OH:20])=[O:19])[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[CH2:13][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:21]O>>[CH3:1][C:2]1[C:7]2[O:8][CH:9]([C:18]([O:20][CH3:21])=[O:19])[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[CH2:13][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 15679048HCID 15679048, compound

Product 1

HCID 15679049HCID 15679049, compound

Procedure

4-Methyl-12H-dibenzo-[d,g][1,3]dioxocin-6-carboxylic acid from Example 1 (1.8 g, 6.6 mmol) was mixed with 75 ml of methanol and 5 g of Dowex™ sulfonic acid resin and the mixture heated at reflux for 16 hours. The mixture was allowed to cool, the resin removed by filtration, and the volatile components removed by evaporation under reduced pressure The residue was taken up in 150 ml of ether and the solution extracted with saturated aqueous sodium bicarbonate and dried over magnesium sulfate. The volatiles were removed by evaporation under reduced pressure and the light yellow residual solid, which amounted to 1.29 g, was recrystallized from ethanol to obtain 0.77 g (41 percent of theory) of the title compound as a solid melting at 104°-105° C. The proton nmr spectrum was consistent with the assigned structure.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 16 hours
  3. temperatureto cool
  4. customthe resin removed by filtration
  5. customthe volatile components removed by evaporation under reduced pressure The residue
  6. extractionthe solution extracted with saturated aqueous sodium bicarbonate
  7. dry with materialdried over magnesium sulfate
  8. customThe volatiles were removed by evaporation under reduced pressure
  9. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-d84aec9e9ecd4f0fb6d08cb71459d6ea
Source dataset
uspto-grants-1990_12
Patent number
US04979978

Reaction notes

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