Hydrochloric Acid → HCID 19088334, compound

HRID 1508774Notes

Reaction equation

HRID 1508774 reaction equation
[CH3:1][C:2]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)([C:9]([O:11]C(C)C)=[O:10])[C:3]([O:5]C(C)C)=[O:4].O1CCOCC1.O.[OH-].[Li+].Cl>C(OCC)(=O)C.O>[CH3:1][C:2]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=1)([C:9]([OH:11])=[O:10])[C:3]([OH:5])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 168937Lithium hydroxide, monohydrateHCID 90112538HCID 90112538, compound

Product 1

HCID 19088334HCID 19088334, compoundYield 106.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

An 250-mL round bottom flask was charged with diisopropyl 2-methyl-2-(4-nitrobenzyl)malonate (1.15 g, 3.55 mmol), dioxane (20 ml) and water (10 ml). To this solution was then added lithium hydroxide monohydrate (0.74 g, 17.8 mmol). The resulting mixture was stirred at 50° C. for 22 h. After this time, the reaction mixture was cooled and acidified with 2N aqueous HCl (10 mL). The mixture was diluted with ethyl acetate (100 mL) and the organic layer washed with saturated sodium chloride (2×10 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the title compound (0.96 g, 100%) as a white solid. MW=253.21. 1H NMR (DMSO-d6, 300 MHz) δ 13.04 (br s, 2H), 8.20-8.12 (m, 2H), 7.49-7.42 (m, 2H), 3.21 (s, 2H), 1.17 (s, 3H).

Workup

  1. temperatureAfter this time, the reaction mixture was cooled
  2. washthe organic layer washed with saturated sodium chloride (2×10 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cfc54bfc047b4e61b96f65b1fba69580
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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