Dimethyl malonate → HCID 18442911, compound

HRID 458708Notes

Reaction equation

HRID 458708 reaction equation
[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([O:14][CH2:15][CH2:16][O:17][C:18]3[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=3)[CH:5]=[CH:4][C:3]1=2.[C:27]([O:34][CH3:35])(=[O:33])[CH2:28][C:29]([O:31][CH3:32])=[O:30].C([O-])(=O)C.[NH2+]1CCCCC1>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([O:14][CH2:15][CH2:16][O:17][C:18]3[CH:19]=[CH:20][C:21]([CH:22]=[C:28]([C:27]([O:34][CH3:35])=[O:33])[C:29]([O:31][CH3:32])=[O:30])=[CH:24][CH:25]=3)[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 3014295Piperidinium acetateHCID 18442907HCID 18442907, compound

Product 1

HCID 18442911HCID 18442911, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4-[2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthoxy)ethoxy]benzaldehyde (1.50 g, 4.26 mmol) and dimethyl malonate (1.69 g, 12.78 mmol) in toluene (30 ml) is added a catalytic quantity of piperidinium acetate. Then the mixture is refluxed in a Dean-Stark trap for 8 hours. After cooled to room temperature, the solution is concentrated under a vacuum to give title compound (1.95 g, 98%).

Workup

  1. temperatureThen the mixture is refluxed in a Dean-Stark trap for 8 hours
  2. concentrationthe solution is concentrated under a vacuum

Sources & evidence

ORD record
ord-21040605a98c4a73bf6395361c3def7a
Source dataset
uspto-grants-2007_03
Patent number
US07192970B2

Reaction notes

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