Sodium Hydroxide → HCID 19812698, compound

HRID 2165023Notes

Reaction equation

HRID 2165023 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:13]3([CH2:15][CH2:14]3)[C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[O:10][CH:9]([C:20]([O:22]C)=[O:21])[O:8][C:7]=2[C:24]=1[O:25][CH3:26].[OH-].[Na+]>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:13]3([CH2:15][CH2:14]3)[C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[O:10][CH:9]([C:20]([OH:22])=[O:21])[O:8][C:7]=2[C:24]=1[O:25][CH3:26]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19812674HCID 19812674, compound

Product 1

HCID 19812698HCID 19812698, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 76 mg (0.23 mmol) of methyl 3',4'-dimethoxyspiro(cyclopropane-1,12'(12'H)-dibenzo[d,g][1,3]dioxocin)-6'-carboxylate in 0.46 ml of tetrahydrofuran was combined with 0.172 ml (0.35 mmol) of 2N aqueous sodium hydroxide and the mixture stirred for 1.3 hour. The resulting mixture was diluted with 0.5 ml of water, extracted with ether, and then acidified with 1N aqueous hydrochloric acid. The resulting mixture was extracted 3 times with 1 ml portions of ether and the combined ethereal extracts were dried over magnesium sulfate and concentrated by evaporation under reduced pressure to obtain the title compound in quantitative yield as a white solid. The proton and carbon NMR and infrared spectra were consistent with the assigned structure.

Workup

  1. extractionextracted with ether
  2. extractionThe resulting mixture was extracted 3 times with 1 ml portions of ether
  3. dry with materialthe combined ethereal extracts were dried over magnesium sulfate
  4. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-556e8f98d3934d9ca795619525572dc1
Source dataset
uspto-grants-1990_07
Patent number
US04938790

Reaction notes

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