Phenol → HCID 86664226, compound

HRID 1184496Notes

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.Br[CH2:23][C:24]([O:26][CH3:27])=[O:25]>>[CH:6]([C:5]1[CH:8]=[C:9]([N+:10]([O-:12])=[O:11])[C:2]([O:1][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[C:3]([O:13][CH3:14])[CH:4]=1)=[O:7]

Participants

Reactant 3

HCID 996Phenol

HCID 60984Methyl bromoacetate

HCID 811345-Nitrovanillin

Product 1

HCID 86664226HCID 86664226, compound

Procedure

Using 4-hydroxy-3-methoxy-5-nitrobenzaldehyde as the phenol and methyl 2-bromoacetate as the alkylating agent in the general procedure for alkylation of substituted 2-nitrophenols gives the title compound as a dark orange oil: 1H NMR (400 MHz, DMSO-d6) δ ppm 3.66 (s, 3H) 3.97 (s, 3 H) 4.98 (s, 2H) 7.83 (d, J=1.77 Hz, 1H) 8.05 (d, J=1.77 Hz, 1H) 9.97 (s, 1H). ESI-MS: m/z 270.1 (M+H)+.

Sources & evidence

ORD record: ord-8a92e7294ceb45d4a4fdb1e719849688
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669249B2

Reaction notes

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