Sodium Hydroxide → HCID 19812698, compound

HRID 359203Notes

Reaction equation

HRID 359203 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 2 N 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 1 N 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-a0645d82729b402e81b9c3eed44ae064
Source dataset
uspto-grants-1991_03
Patent number
US04999448

Reaction notes

Loading…