Sodium Hydroxide → HCID 22151946, compound

HRID 1111288Notes

Reaction equation

HRID 1111288 reaction equation
C[O:2][C:3]([CH:5]1[O:12][C:11]2[CH:13]=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:10]=2[CH2:9][C:8]2[CH:19]=[CH:20][CH:21]=[CH:22][C:7]=2[O:6]1)=[O:4].[OH-].[Na+]>O1CCCC1.O.CCOCC>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:10]2[CH2:9][C:8]3[CH:19]=[CH:20][CH:21]=[CH:22][C:7]=3[O:6][CH:5]([C:3]([OH:4])=[O:2])[O:12][C:11]=2[CH:13]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 22151967HCID 22151967, compound

Product 1

HCID 22151946HCID 22151946, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl-3-methoxy-12H-dibenzo[d,g][1,3]-dioxocin-6-carboxylate (0.32 g, 1.07 mmol) was dissolved in 20 ml of tetrahydrofuran and 3.0 ml of 2 M sodium hydroxide was added. The mixture was stirred at ambient temperature overnight. It was then diluted with 20 ml of water and 50 ml of ether and the layers separated. The organic layer was extracted with water and the aqueous extract combined with the original aqueous layer. The resulting solution was acidified with 10 percent aqueous hydrochloric acid and then extracted with 4-25 ml portions of ether. The combined ether extracts were dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain the title compound as a yellow-white foamed solid amounting to 0.26 g (85 percent of theory) and melting at 149°-153° C. The proton nmr spectrum was consistent with the assigned structure.

Workup

  1. customthe layers separated
  2. extractionThe organic layer was extracted with water
  3. extractionthe aqueous extract
  4. extractionextracted with 4-25 ml portions of ether
  5. dry with materialThe combined ether extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-1d8604ea98d242f6952f9c4000f94a75
Source dataset
uspto-grants-1990_12
Patent number
US04979978

Reaction notes

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