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

HRID 2083184Notes

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

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 hr 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, mp 74°-76° C.

Workup

additionwas added dropwise
stirringThe reaction mixture was stirred overnight
custombrought to room temperature
filtrationThe mixture was filtered
customsolvent was removed from the filtrate by evaporation
customThe residue was recrystallized from methanol

Sources & evidence

ORD record: ord-bab99319dc864014a9b8c6d87f199a4c
Source dataset: uspto-grants-1978_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04085091

Reaction notes

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