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

HRID 462026Notes

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 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

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-9405828848b34da78ac5aedf9ea9d593
Source dataset: uspto-grants-1977_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04065431

Reaction notes

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