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

HRID 1042617Notes

Reaction equation

HRID 1042617 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 are 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 tetrahydrofurane:water 9:1. The mixture is 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 is partitioned between water and ethyl acetate; the organic phase is 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 is used without further purification.

Workup

  1. customto react for 21.5 hours at 25° C.
  2. customThe mixture is partitioned between water and ethyl acetate
  3. washthe organic phase is 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 is used without further purification

Sources & evidence

ORD record
ord-8c78acdd69ff4c5e94680c2c29ef392a
Source dataset
uspto-grants-2013_10
Patent number
US08557922B2

Reaction notes

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