Phenol → HCID 54941441, compound

HRID 1184423Notes

Reaction equation

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

Participants

Reactant 3

HCID 996Phenol

HCID 181694-Hydroxy-3-nitrobenzaldehyde

HCID 95576Methyl 2-bromopropionate

Product 1

HCID 54941441HCID 54941441, compoundYield 61%

Procedure

Using 4-hydroxy-3-nitrobenzaldehyde as the phenol and methyl-2-bromopropanoate as the alkylating agent in the general procedure for alkylation of substituted-2-nitrophenols gives a light yellow solid (1.55 g, 61% yield): 1H NMR (400 MHz, DMSO-d6) δ ppm 1.57 (d, J=6.82 Hz, 3H) 3.70 (s, 3H) 5.46 (q, J=6.65 Hz, 1H) 7.45 (d, J=8.84 Hz, 1H) 8.13 (d, J=8.84 Hz, 1H) 8.43 (s, 1H) 9.94 (s, 1 H). ESI-MS: m/z 254.1 (M+H)+.

Sources & evidence

ORD record: ord-6ce4d5804e9d4ccdbc07ce49fd89054c
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669249B2

Reaction notes

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