Diethyl Malonate → Diethyl 2-[(4-octylphenyl)methylene]propanedioate

HRID 1198216Notes

Reaction equation

[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH2:12]([C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>N1CCCCC1>[CH2:12]([C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])=[CH:22][CH:21]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

Conditions

Temperature: 100 °C

Procedure

Diethyl malonate (1.76g, 0.011 moles), paraoctylbenzaldehyde (2.4g, 0.011 moles) and piperidine (5 drops) were heated to 98° C. for 2.5 hrs. and 45° C. for 16 hrs. The solution was heated to 100° C. for 64 hrs. The title compound was purified by silica gel chromatography. The structure assignment was supported by NMR, infrared and uv spectra and elemental analysis (360.5).

Workup

customThe title compound was purified by silica gel chromatography

Sources & evidence

ORD record: ord-5af11e0ea1b04ddd8ec610c4fed85d0d
Source dataset: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05280047

Reaction notes

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