Diisopropylamine → 1,4-Bis(2-carbomethoxy-2-methylpropyl)benzene

HRID 971913Notes

Reaction equation

HRID 971913 reaction equation
C(N[CH:5]([CH3:7])[CH3:6])(C)C.C([Li])CCC.[C:13]([O:18][CH3:19])(=[O:17])[CH:14]([CH3:16])[CH3:15].Br[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28]Br)=[CH:24][CH:23]=1>CCCCCC.O1CCCC1>[C:13]([C:5]([CH3:6])([CH3:7])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:14]([CH3:16])([C:13]([O:18][CH3:19])=[O:17])[CH3:15])=[CH:24][CH:23]=1)([O:18][CH3:19])=[O:17]

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 11039Methyl isobutyrateHCID 693351,4-Bis(bromomethyl)benzeneHCID 178418339Butyllithium

Product 1

HCID 213125761,4-Bis(2-carbomethoxy-2-methylpropyl)benzeneYield 86.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

To 1 liter of dry tetrahydrofuran was added 52 g of diisopropylamine. The mixture was cooled to -78° C. and 325 ml of 1.6 M n-butyllithium in hexane was added. After 1 hour of stirring 52 g of methyl isobutyrate was added dropwise followed by stirring for another 30 minutes. Then 63 g of α,α'-dibromo-p-xylene was slowly added. The reaction mixture was stirred overnight and brought to room temperature. The mixture was filtered and solvent was removed from the filtrate by evaporation. The residue was recrystallized from methanol to obtain 63 g of 1,4-bis(2-carbomethoxy-2-methylpropyl)benzene, m.p. 74°-76° C.

Workup

  1. additionwas added dropwise
  2. stirringThe reaction mixture was stirred overnight
  3. custombrought to room temperature
  4. filtrationThe mixture was filtered
  5. customsolvent was removed from the filtrate by evaporation
  6. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-a8576a09ff17453b896866f76c58a23f
Source dataset
uspto-grants-1979_07
Patent number
US04161607

Reaction notes

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