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Sulfuric Acid → 4-tert.butyl 1-(4nitrobenzyl) 2(R)-isobutylsuccinate

HRID 982566
Notes
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Reaction equation

HRID 982566 reaction equation
[CH2:1]([C@H:5]([CH2:19][C:20]([OH:22])=[O:21])[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)=[O:7])[CH:2]([CH3:4])[CH3:3].[CH2:23]=[C:24]([CH3:26])[CH3:25].S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>C(OCC)C.O>[CH2:1]([C@H:5]([CH2:19][C:20]([O:22][C:24]([CH3:26])([CH3:25])[CH3:23])=[O:21])[C:6]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([N+:16]([O-:18])=[O:17])=[CH:14][CH:15]=1)=[O:7])[CH:2]([CH3:4])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 516892Sodium BicarbonateHCID 541390571-(4-nitrobenzyl) hydrogen 2(R)-isobutylsuccinate

Product 1

HCID 585602894-tert.butyl 1-(4nitrobenzyl) 2(R)-isobutylsuccinateYield 77%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 3283Diethyl EtherSolvent

Procedure

9.4 g of 1-(4-nitrobenzyl) hydrogen 2(R)-isobutylsuccinate were dissolved in 30 ml of dry diethyl ether and the solution was cooled in a dry-ice/acetone bath. There were then added 70 ml of isobutene, followed dropwise by 0.64 ml of concentrated sulfuric acid. The reaction flask was tightly topped and the mixture was stirred at room temperature for 2 days. The mixture was made basic with saturated sodium hydrogen carbonate solution and water was added. The organic phase was separated and the aqueous phase was extracted twice more with diethyl ether. The combined ethereal phases were washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and evaporated to give 8.8 g (77%) of 4-tert.butyl 1-(4nitrobenzyl) 2(R)-isobutylsuccinate in the form of an oil. Rf (System A) 0.87.

Workup

  1. temperaturethe solution was cooled in a dry-ice/acetone bath
  2. additionwas added
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted twice more with diethyl ether
  5. washThe combined ethereal phases were washed with water and saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-6729c9e341df48cdbdffa3a3b1bce6ea
Source dataset
uspto-grants-1991_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04996358

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes