Hydrochloric Acid → 2,2-Bis(4-nitrobenzyl)malonic acid

HRID 2090146Notes

Reaction equation

HRID 2090146 reaction equation
[OH-].[Li+].CC1(C)[O:9][C:8](=[O:10])[C:7]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[C:6](=[O:31])[O:5]1.O1CCCC1.O.Cl>O>[N+:18]([C:15]1[CH:14]=[CH:13][C:12]([CH2:11][C:7]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][CH:23]=2)([C:6]([OH:31])=[O:5])[C:8]([OH:10])=[O:9])=[CH:17][CH:16]=1)([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 46194582,2-Dimethyl-5,5-bis(4-nitrobenzyl)-1,3-dioxane-4,6-dioneHCID 21881883Oxolane--water (1/1)

Product 1

HCID 229285922,2-Bis(4-nitrobenzyl)malonic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.185 g (52.07 mmol) of lithium hydroxide were added to a suspension of 10.79 g (26.04 mmol) of 2,2-dimethyl-5,5-bis(4-nitrobenzyl)-1,3-dioxane-4,6-dione and 110 ml mixture of tetrahydrofuran:water 9:1. The mixture was subsequently allowed to react for 21.5 hours at 25° C., added to 500 ml water and acidified to pH=1 with 20 ml hydrochloric acid 3N. The mixture was partitioned between water and ethyl acetate; the organic phase was washed repeatedly with water, dried over sodium sulfate, filtered and concentrated by rotary evaporation. The residue 9.54 g (98%) of 2,2-bis(4-nitrobenzyl)malonic acid as white powder was used without further purification.

Workup

  1. customto react for 21.5 hours at 25° C.
  2. customThe mixture was partitioned between water and ethyl acetate
  3. washthe organic phase was washed repeatedly with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation
  7. customThe residue 9.54 g (98%) of 2,2-bis(4-nitrobenzyl)malonic acid as white powder was used without further purification

Sources & evidence

ORD record
ord-78d868f982a24ed69c0f95801c546905
Source dataset
uspto-grants-2013_05
Patent number
US08436132B2

Reaction notes

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