Morpholine → HCID 86743564, compound

HRID 476822Notes

Reaction equation

HRID 476822 reaction equation
[C:1]([O:14][CH2:15][C:16]([CH3:20])([CH3:19])[CH:17]=[O:18])(=[O:13])/[CH:2]=[CH:3]\[C:4]([O:6][CH2:7][C:8]([CH3:12])([CH3:11])[CH:9]=[O:10])=[O:5].N1CCOCC1>C1(C)C=CC=CC=1>[C:1]([O:14][CH2:15][C:16]([CH3:20])([CH3:19])[CH:17]=[O:18])(=[O:13])/[CH:2]=[CH:3]/[C:4]([O:6][CH2:7][C:8]([CH3:11])([CH3:12])[CH:9]=[O:10])=[O:5]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 86743565HCID 86743565, compound

Product 1

HCID 86743564HCID 86743564, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Crude bis (2,2-dimethyl-3-oxopropyl) maleate was treated with a catalytic amount of morpholine (10 wt. %) in refluxing toluene for 4 hrs. The resulting solution was cooled to room temperature, washed with diluted hydrochloric acid and brine, then dried over magnesium sulfate. Evaporation of volatiles in vacuo gave crud bis (2,2-dimethyl-3-oxopropyl) fumarate in essentially quantitative yield. NMR* (CDCL3): 9.7 (s, 1H,--CHO), 6.93 (s, 2H, trans --CH=CH--), 4.33 (s, 2H, --CO2CH2 --), and 1.2 (s, 6H, --C(CH3)2 --).

Workup

  1. washwashed with diluted hydrochloric acid and brine
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation of volatiles in vacuo

Sources & evidence

ORD record
ord-575eacd8588941dd83432dd6a7b9eeac
Source dataset
uspto-grants-1989_12
Patent number
US04886618

Reaction notes

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