Phenol → HCID 71813481, compound

HRID 1184426Notes

Reaction equation

[OH:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:13][CH3:14].C1(O)C=CC=CC=1.[CH3:22][O:23][C:24](=[O:28])[CH:25](Br)[CH3:26]>>[CH:6]([C:5]1[CH:8]=[C:9]([N+:10]([O-:12])=[O:11])[C:2]([O:1][CH:25]([CH3:26])[C:24]([O:23][CH3:22])=[O:28])=[C:3]([O:13][CH3:14])[CH:4]=1)=[O:7]

Participants

Reactant 3

HCID 996Phenol

HCID 811345-Nitrovanillin

HCID 95576Methyl 2-bromopropionate

Product 1

HCID 71813481HCID 71813481, compound

Procedure

Using 4-hydroxy-3-methoxy-5-nitrobenzaldehyde as the phenol and methyl-2-bromopropanoate as the alkylating agent in the general procedure for alkylation of substituted-2-nitrophenols gives a dark oil: 1H NMR (DMSO-d6, 400 MHz): δ ppm 9.95 (s, 1H), 8.03 (d, J=1.8 Hz, 1H), 7.80 (d, J=1.8 Hz, 1 H), 5.15 (q, J=6.8 Hz, 1H), 3.95 (s, 3H), 3.63 (s, 3H), 1.50 (d, J=6.8 Hz, 3H). ESI-MS: m/z 284.1 (M+H)+.

Workup

customgives a dark oil

Sources & evidence

ORD record: ord-884e5dab3c384164b3ae5e920110b696
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669249B2

Reaction notes

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