Sodium Hydroxide → HCID 19353308, compound

HRID 378254Notes

Reaction equation

HRID 378254 reaction equation
[CH3:1][O:2][C:3]1[C:15]([C:16]([O:18]C)=[O:17])=[C:14]([C:20]([O:22]C)=O)[C:13]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)=[C:12]2[C:4]=1[CH:5]=[CH:6][C:7]1[O:11][CH2:10][O:9][C:8]=12.[OH-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[C:15]2[C:16](=[O:17])[O:18][C:20](=[O:22])[C:14]=2[C:13]([C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)=[C:12]2[C:4]=1[CH:5]=[CH:6][C:7]1[O:11][CH2:10][O:9][C:8]=12

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19353248HCID 19353248, compound

Product 1

HCID 19353308HCID 19353308, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

To an ethanol (10Oml) solution of dimethyl 6-methoxy-9-(4-methoxyphenyl)-naphtho[1,2-d]-1,3-dioxole-7,8-dicarboxylate (2.33 g, 5.04 mmol) was added 4N sodium hydroxide solution (10 ml) and heated under reflux for 2 hours. Ethanol was distilled off under reduced pressure. Concentrated hydrochloric acid was added to the residue to adjust the pH of the mixture to about 1 and extracted with THF-ethyl acetate(1:1) twice. The organic layer was washed with saturated sodium chloride solution and dried with magnesium sulfate, then the solvent was distilled off under reduced pressure. The obtained residue was heated for 10 minutes at 150° C. to give crude crystals of 6-methoxy-10-(4-methoxyphenyl)-furo[3',4':6,7]naphtho[1,2-d]-1,3-dioxol-7,9-dione.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. distillationEthanol was distilled off under reduced pressure
  4. additionConcentrated hydrochloric acid was added to the residue
  5. extractionextracted with THF-ethyl acetate(1:1) twice
  6. washThe organic layer was washed with saturated sodium chloride solution
  7. dry with materialdried with magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-dc0b30be88634b4b8726c17e8f199e8f
Source dataset
uspto-grants-2000_02
Patent number
US06030967

Reaction notes

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