N-Methylaniline → tetra-(hydroxymethyl)methane tetra-(3-[N-methyl-N-phenylamino]propionate)

HRID 1848398

Reaction equation

[C:1]([O:5][CH2:6][C:7]([CH2:20][O:21][C:22](=[O:25])[CH:23]=[CH2:24])([CH2:14][O:15]C(=O)C=C)[CH2:8][O:9]C(=O)C=C)(=[O:4])[CH:2]=[CH2:3].[CH3:26][NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(O)(=O)C>[CH3:26][N:27]([CH2:24][CH2:23][C:22]([OH:21])=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[CH3:26][N:27]([CH2:3][CH2:2][C:1]([OH:5])=[O:4])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[CH3:26][N:27]([CH2:24][CH2:23][C:22]([OH:21])=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[CH3:26][N:27]([CH2:24][CH2:23][C:22]([OH:21])=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[OH:5][CH2:6][C:7]([CH2:20][OH:21])([CH2:14][OH:15])[CH2:8][OH:9]

Participants

Conditions

Temperature: 100 °C

Procedure

Pentaerythritol tetraacrylate (4.4 g, 0.0125 moles) was added to N-methylaniline (5.4 g 0.050 moles), dissolved in glacial acetic acid (10 ml). The mixture was heated with stirring at 100° C. for 2 hours and then the acetic acid removed by vacuum distillation. An infrared spectrum of the residual oil revealed the presence of a little unreacted N-methylaniline but little sign of any unreacted acrylate groups. Absorptions due to the presence of a saturated ester (1730 cm−1) and an aromatic amine (1600 cm−) were found. 1H NMR δ 2.6 (CH2—CO, 8H t), 2.9 (CH3—N 12H s) 3.6 (CH2—N, 8H, t), 4.1 (CH2—O 8H s), 6.7 (aromatic protons 12H) 7.2 (aromatic protons 8H).

Workup

temperatureThe mixture was heated
customthe acetic acid removed by vacuum distillation

Sources & evidence

ORD record: ord-c2315b66599847e7bae1f0631c346249
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952190B2

Linked notes

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