Phenol → HCID 62116070, compound

HRID 1184429Notes

Reaction equation

HRID 1184429 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH:5]=[O:6].C1(O)C=CC=CC=1.[CH3:20][O:21][C:22](=[O:26])[CH:23](Br)[CH3:24]>>[CH:5]([C:4]1[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:2]([CH:3]=1)[O:1][CH:23]([CH3:24])[C:22]([O:21][CH3:20])=[O:26])=[O:6]

Participants

4

Reactant 3

HCID 996PhenolHCID 697123-Hydroxy-4-nitrobenzaldehydeHCID 95576Methyl 2-bromopropionate

Product 1

HCID 62116070HCID 62116070, compound

Procedure

Using 3-hydroxy-4-nitrobenzaldehyde as the phenol and methyl-2-bromopropanoate as the alkylating agent in the general procedure for alkylation of substituted-2-nitrophenols gives a tan solid: 1H NMR (DMSO-d6, 400 MHz): δ ppm 10.03 (s, 1H), 8.08 (d, J=8.1 Hz, 1H), 7.62-7.79 (m, 2H), 5.43 (q, J=6.8 Hz, 1H), 3.69 (s, 3H), 1.55 (d, J=6.8 Hz, 3H). ESI-MS: m/z 254.1 (M+H)+.

Workup

  1. customgives a tan solid

Sources & evidence

ORD record
ord-2da28915e4684e47ae33bda5b4870ba6
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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