Phenol → HCID 71813140, compound

HRID 1184444Notes

Reaction equation

HRID 1184444 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:27])[CH:23](Br)[CH2:24][CH3:25]>>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH:23]([CH2:24][CH3:25])[C:22]([O:21][CH3:20])=[O:27])=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=1)=[O:7]

Participants

4

Reactant 3

HCID 996PhenolHCID 181694-Hydroxy-3-nitrobenzaldehydeHCID 95577Butanoic acid, 2-bromo-, methyl ester

Product 1

HCID 71813140HCID 71813140, compound

Procedure

Using 4-hydroxy-3-nitrobenzaldehyde as the phenol and methyl-2-bromobutanoate as the alkylating agent in the general procedure of alkylation of substituted 2-nitrophenols gives a clear yellow oil: 1H NMR (DMSO-d6, 400 MHz): δ=9.94 (s, 1H), 8.44 (d, J=2.3 Hz, 1H), 8.13 (dd, J=8.8, 2.0 Hz, 1H), 7.42 (d, J=8.8 Hz, 1H), 5.36 (dd, J=6.6, 4.5 Hz, 1H), 3.70 (s, 3H), 1.88-2.05 (m, 2H), 0.98 ppm (t, J=7.5 Hz, 3H). ESI-MS: m/z 268.2 (M+H)+.

Workup

  1. customgives a clear yellow oil

Sources & evidence

ORD record
ord-09081b6cd0a942d3be2891974a88e68a
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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